id sid tid token lemma pos 08612n51m2b 1 1 this this DET 08612n51m2b 1 2 dissertation dissertation NOUN 08612n51m2b 1 3 comprises comprise VERB 08612n51m2b 1 4 two two NUM 08612n51m2b 1 5 major major ADJ 08612n51m2b 1 6 components component NOUN 08612n51m2b 1 7 that that PRON 08612n51m2b 1 8 sequentially sequentially ADV 08612n51m2b 1 9 describe describe VERB 08612n51m2b 1 10 literature literature NOUN 08612n51m2b 1 11 reviews review NOUN 08612n51m2b 1 12 pertinent pertinent ADJ 08612n51m2b 1 13 to to ADP 08612n51m2b 1 14 tetrahydropyran tetrahydropyran NOUN 08612n51m2b 1 15 - - PUNCT 08612n51m2b 1 16 containing contain VERB 08612n51m2b 1 17 small small ADJ 08612n51m2b 1 18 macrolides macrolide NOUN 08612n51m2b 1 19 of of ADP 08612n51m2b 1 20 cyanobacterial cyanobacterial ADJ 08612n51m2b 1 21 origins origin NOUN 08612n51m2b 1 22 and and CCONJ 08612n51m2b 1 23 research research NOUN 08612n51m2b 1 24 in in ADP 08612n51m2b 1 25 the the DET 08612n51m2b 1 26 field field NOUN 08612n51m2b 1 27 of of ADP 08612n51m2b 1 28 synthetic synthetic ADJ 08612n51m2b 1 29 organic organic ADJ 08612n51m2b 1 30 chemistry chemistry NOUN 08612n51m2b 1 31 that that PRON 08612n51m2b 1 32 demonstrates demonstrate VERB 08612n51m2b 1 33 synthetic synthetic ADJ 08612n51m2b 1 34 methodology methodology NOUN 08612n51m2b 1 35 development development NOUN 08612n51m2b 1 36 directed direct VERB 08612n51m2b 1 37 for for ADP 08612n51m2b 1 38 stereoselective stereoselective ADJ 08612n51m2b 1 39 production production NOUN 08612n51m2b 1 40 of of ADP 08612n51m2b 1 41 highly highly ADV 08612n51m2b 1 42 functionalized functionalize VERB 08612n51m2b 1 43 oxacycles oxacycle NOUN 08612n51m2b 1 44 and and CCONJ 08612n51m2b 1 45 their their PRON 08612n51m2b 1 46 applications application NOUN 08612n51m2b 1 47 in in ADP 08612n51m2b 1 48 complex complex ADJ 08612n51m2b 1 49 molecule molecule NOUN 08612n51m2b 1 50 synthesis synthesis NOUN 08612n51m2b 1 51 . . PUNCT 08612n51m2b 2 1 the the DET 08612n51m2b 2 2 research research NOUN 08612n51m2b 2 3 discussion discussion NOUN 08612n51m2b 2 4 commences commence VERB 08612n51m2b 2 5 with with ADP 08612n51m2b 2 6 a a DET 08612n51m2b 2 7 systematic systematic ADJ 08612n51m2b 2 8 study study NOUN 08612n51m2b 2 9 towards towards ADP 08612n51m2b 2 10 the the DET 08612n51m2b 2 11 total total ADJ 08612n51m2b 2 12 synthesis synthesis NOUN 08612n51m2b 2 13 of of ADP 08612n51m2b 2 14 ( ( PUNCT 08612n51m2b 2 15 + + NOUN 08612n51m2b 2 16 ) ) PUNCT 08612n51m2b 2 17 -acutiphycin -acutiphycin PROPN 08612n51m2b 2 18 , , PUNCT 08612n51m2b 2 19 a a DET 08612n51m2b 2 20 highly highly ADV 08612n51m2b 2 21 cytotoxic cytotoxic ADJ 08612n51m2b 2 22 macrolide macrolide NOUN 08612n51m2b 2 23 with with ADP 08612n51m2b 2 24 an an DET 08612n51m2b 2 25 unknown unknown ADJ 08612n51m2b 2 26 mode mode NOUN 08612n51m2b 2 27 of of ADP 08612n51m2b 2 28 action action NOUN 08612n51m2b 2 29 . . PUNCT 08612n51m2b 3 1 our our PRON 08612n51m2b 3 2 convergent convergent ADJ 08612n51m2b 3 3 route route NOUN 08612n51m2b 3 4 was be AUX 08612n51m2b 3 5 highlighted highlight VERB 08612n51m2b 3 6 by by ADP 08612n51m2b 3 7 an an DET 08612n51m2b 3 8 extensive extensive ADJ 08612n51m2b 3 9 utilization utilization NOUN 08612n51m2b 3 10 of of ADP 08612n51m2b 3 11 the the DET 08612n51m2b 3 12 vinylogous vinylogous ADJ 08612n51m2b 3 13 mukaiyama mukaiyama PROPN 08612n51m2b 3 14 aldol aldol PROPN 08612n51m2b 3 15 reactions reaction NOUN 08612n51m2b 3 16 for for ADP 08612n51m2b 3 17 the the DET 08612n51m2b 3 18 construction construction NOUN 08612n51m2b 3 19 of of ADP 08612n51m2b 3 20 both both DET 08612n51m2b 3 21 southern southern ADJ 08612n51m2b 3 22 and and CCONJ 08612n51m2b 3 23 northern northern ADJ 08612n51m2b 3 24 hemispheres hemisphere NOUN 08612n51m2b 3 25 of of ADP 08612n51m2b 3 26 the the DET 08612n51m2b 3 27 macrolide macrolide NOUN 08612n51m2b 3 28 . . PUNCT 08612n51m2b 4 1 the the DET 08612n51m2b 4 2 acutiphycin acutiphycin PROPN 08612n51m2b 4 3 study study NOUN 08612n51m2b 4 4 concluded conclude VERB 08612n51m2b 4 5 with with ADP 08612n51m2b 4 6 a a DET 08612n51m2b 4 7 thorough thorough ADJ 08612n51m2b 4 8 investigation investigation NOUN 08612n51m2b 4 9 of of ADP 08612n51m2b 4 10 aldol aldol PROPN 08612n51m2b 4 11 - - PUNCT 08612n51m2b 4 12 mediated mediate VERB 08612n51m2b 4 13 advanced advanced ADJ 08612n51m2b 4 14 fragments fragment NOUN 08612n51m2b 4 15 coupling coupling NOUN 08612n51m2b 4 16 strategy strategy NOUN 08612n51m2b 4 17 . . PUNCT 08612n51m2b 5 1 our our PRON 08612n51m2b 5 2 research research NOUN 08612n51m2b 5 3 continues continue VERB 08612n51m2b 5 4 with with ADP 08612n51m2b 5 5 the the DET 08612n51m2b 5 6 development development NOUN 08612n51m2b 5 7 of of ADP 08612n51m2b 5 8 electrophile electrophile NOUN 08612n51m2b 5 9 - - PUNCT 08612n51m2b 5 10 induced induce VERB 08612n51m2b 5 11 ether ether NOUN 08612n51m2b 5 12 transfer transfer NOUN 08612n51m2b 5 13 reaction reaction NOUN 08612n51m2b 5 14 . . PUNCT 08612n51m2b 6 1 this this DET 08612n51m2b 6 2 novel novel ADJ 08612n51m2b 6 3 synthetic synthetic ADJ 08612n51m2b 6 4 method method NOUN 08612n51m2b 6 5 readily readily ADV 08612n51m2b 6 6 generated generate VERB 08612n51m2b 6 7 1,3 1,3 PROPN 08612n51m2b 6 8 - - PUNCT 08612n51m2b 6 9 syn syn PROPN 08612n51m2b 6 10 diol diol PROPN 08612n51m2b 6 11 monoether monoether PROPN 08612n51m2b 6 12 , , PUNCT 08612n51m2b 6 13 a a DET 08612n51m2b 6 14 common common ADJ 08612n51m2b 6 15 functionality functionality NOUN 08612n51m2b 6 16 in in ADP 08612n51m2b 6 17 polyketide polyketide NOUN 08612n51m2b 6 18 that that PRON 08612n51m2b 6 19 presents present VERB 08612n51m2b 6 20 a a DET 08612n51m2b 6 21 significant significant ADJ 08612n51m2b 6 22 synthetic synthetic ADJ 08612n51m2b 6 23 challenge challenge NOUN 08612n51m2b 6 24 . . PUNCT 08612n51m2b 7 1 this this DET 08612n51m2b 7 2 transformation transformation NOUN 08612n51m2b 7 3 was be AUX 08612n51m2b 7 4 accomplished accomplish VERB 08612n51m2b 7 5 by by ADP 08612n51m2b 7 6 simply simply ADV 08612n51m2b 7 7 exposing expose VERB 08612n51m2b 7 8 homoallylic homoallylic ADJ 08612n51m2b 7 9 alkoxymethyl alkoxymethyl NOUN 08612n51m2b 7 10 ether ether PROPN 08612n51m2b 7 11 to to ADP 08612n51m2b 7 12 iodine iodine NOUN 08612n51m2b 7 13 monochloride monochloride PROPN 08612n51m2b 7 14 . . PUNCT 08612n51m2b 8 1 the the DET 08612n51m2b 8 2 reaction reaction NOUN 08612n51m2b 8 3 mechanism mechanism NOUN 08612n51m2b 8 4 was be AUX 08612n51m2b 8 5 proposed propose VERB 08612n51m2b 8 6 via via ADP 08612n51m2b 8 7 an an DET 08612n51m2b 8 8 intermediacy intermediacy NOUN 08612n51m2b 8 9 of of ADP 08612n51m2b 8 10 chloromethyl chloromethyl PROPN 08612n51m2b 8 11 ether ether PROPN 08612n51m2b 8 12 as as SCONJ 08612n51m2b 8 13 observed observe VERB 08612n51m2b 8 14 by by ADP 08612n51m2b 8 15 in in ADP 08612n51m2b 8 16 situ situ ADJ 08612n51m2b 8 17 nmr nmr NOUN 08612n51m2b 8 18 experiments experiment NOUN 08612n51m2b 8 19 . . PUNCT 08612n51m2b 9 1 the the DET 08612n51m2b 9 2 ability ability NOUN 08612n51m2b 9 3 to to PART 08612n51m2b 9 4 quench quench VERB 08612n51m2b 9 5 the the DET 08612n51m2b 9 6 chloromethyl chloromethyl NOUN 08612n51m2b 9 7 ether ether NOUN 08612n51m2b 9 8 intermediate intermediate ADJ 08612n51m2b 9 9 with with ADP 08612n51m2b 9 10 various various ADJ 08612n51m2b 9 11 nucleophiles nucleophile NOUN 08612n51m2b 9 12 , , PUNCT 08612n51m2b 9 13 such such ADJ 08612n51m2b 9 14 as as ADP 08612n51m2b 9 15 cyanide cyanide NOUN 08612n51m2b 9 16 or or CCONJ 08612n51m2b 9 17 thiophenol thiophenol NOUN 08612n51m2b 9 18 , , PUNCT 08612n51m2b 9 19 showcased showcase VERB 08612n51m2b 9 20 the the DET 08612n51m2b 9 21 versatility versatility NOUN 08612n51m2b 9 22 of of ADP 08612n51m2b 9 23 the the DET 08612n51m2b 9 24 ether ether NOUN 08612n51m2b 9 25 transfer transfer NOUN 08612n51m2b 9 26 reaction reaction NOUN 08612n51m2b 9 27 . . PUNCT 08612n51m2b 10 1 this this DET 08612n51m2b 10 2 strategy strategy NOUN 08612n51m2b 10 3 readily readily ADV 08612n51m2b 10 4 yielded yield VERB 08612n51m2b 10 5 precursors precursor NOUN 08612n51m2b 10 6 for for ADP 08612n51m2b 10 7 the the DET 08612n51m2b 10 8 production production NOUN 08612n51m2b 10 9 of of ADP 08612n51m2b 10 10 six six NUM 08612n51m2b 10 11 - - PUNCT 08612n51m2b 10 12 membered membered ADJ 08612n51m2b 10 13 oxygen oxygen NOUN 08612n51m2b 10 14 heterocycles heterocycle NOUN 08612n51m2b 10 15 via via ADP 08612n51m2b 10 16 a a DET 08612n51m2b 10 17 general general ADJ 08612n51m2b 10 18 three three NUM 08612n51m2b 10 19 - - PUNCT 08612n51m2b 10 20 step step NOUN 08612n51m2b 10 21 sequence sequence NOUN 08612n51m2b 10 22 : : PUNCT 08612n51m2b 10 23 ether ether NOUN 08612n51m2b 10 24 transfer transfer NOUN 08612n51m2b 10 25 , , PUNCT 08612n51m2b 10 26 cyclization cyclization NOUN 08612n51m2b 10 27 , , PUNCT 08612n51m2b 10 28 and and CCONJ 08612n51m2b 10 29 functionalization functionalization NOUN 08612n51m2b 10 30 reactions reaction NOUN 08612n51m2b 10 31 . . PUNCT 08612n51m2b 11 1 depending depend VERB 08612n51m2b 11 2 upon upon SCONJ 08612n51m2b 11 3 the the DET 08612n51m2b 11 4 functionalization functionalization NOUN 08612n51m2b 11 5 step step NOUN 08612n51m2b 11 6 , , PUNCT 08612n51m2b 11 7 a a DET 08612n51m2b 11 8 robust robust ADJ 08612n51m2b 11 9 production production NOUN 08612n51m2b 11 10 of of ADP 08612n51m2b 11 11 stereocomplementary stereocomplementary ADJ 08612n51m2b 11 12 4 4 NUM 08612n51m2b 11 13 - - PUNCT 08612n51m2b 11 14 alkoxy-2,6 alkoxy-2,6 NOUN 08612n51m2b 11 15 - - PUNCT 08612n51m2b 11 16 cisand cisand NOUN 08612n51m2b 11 17 trans trans ADJ 08612n51m2b 11 18 - - ADJ 08612n51m2b 11 19 disubstituted disubstitute VERB 08612n51m2b 11 20 tetrahydropyrans tetrahydropyran NOUN 08612n51m2b 11 21 and and CCONJ 08612n51m2b 11 22 trans-2,6 trans-2,6 PROPN 08612n51m2b 11 23 - - PUNCT 08612n51m2b 11 24 disubstituted-3,4 disubstituted-3,4 ADJ 08612n51m2b 11 25 - - PUNCT 08612n51m2b 11 26 dihydropyrans dihydropyran NOUN 08612n51m2b 11 27 was be AUX 08612n51m2b 11 28 successfully successfully ADV 08612n51m2b 11 29 achieved achieve VERB 08612n51m2b 11 30 in in ADP 08612n51m2b 11 31 a a DET 08612n51m2b 11 32 stereoselective stereoselective ADJ 08612n51m2b 11 33 fashion fashion NOUN 08612n51m2b 11 34 . . PUNCT 08612n51m2b 12 1 these these DET 08612n51m2b 12 2 methods method NOUN 08612n51m2b 12 3 were be AUX 08612n51m2b 12 4 then then ADV 08612n51m2b 12 5 successfully successfully ADV 08612n51m2b 12 6 applied apply VERB 08612n51m2b 12 7 to to ADP 08612n51m2b 12 8 an an DET 08612n51m2b 12 9 efficient efficient ADJ 08612n51m2b 12 10 construction construction NOUN 08612n51m2b 12 11 of of ADP 08612n51m2b 12 12 the the DET 08612n51m2b 12 13 oxacycle oxacycle ADJ 08612n51m2b 12 14 core core NOUN 08612n51m2b 12 15 of of ADP 08612n51m2b 12 16 phorboxazole phorboxazole PROPN 08612n51m2b 12 17 a a DET 08612n51m2b 12 18 and and CCONJ 08612n51m2b 12 19 swinholide swinholide PROPN 08612n51m2b 12 20 a. a. PROPN 08612n51m2b 12 21 our our PRON 08612n51m2b 12 22 final final ADJ 08612n51m2b 12 23 research research NOUN 08612n51m2b 12 24 project project NOUN 08612n51m2b 12 25 describes describe VERB 08612n51m2b 12 26 a a DET 08612n51m2b 12 27 concise concise ADJ 08612n51m2b 12 28 enantioselective enantioselective ADJ 08612n51m2b 12 29 total total ADJ 08612n51m2b 12 30 synthesis synthesis NOUN 08612n51m2b 12 31 of of ADP 08612n51m2b 12 32 neopeltolide neopeltolide ADJ 08612n51m2b 12 33 macrolactone macrolactone NOUN 08612n51m2b 12 34 . . PUNCT 08612n51m2b 13 1 the the DET 08612n51m2b 13 2 successful successful ADJ 08612n51m2b 13 3 synthetic synthetic ADJ 08612n51m2b 13 4 approach approach NOUN 08612n51m2b 13 5 was be AUX 08612n51m2b 13 6 highlighted highlight VERB 08612n51m2b 13 7 by by ADP 08612n51m2b 13 8 sequential sequential ADJ 08612n51m2b 13 9 utilization utilization NOUN 08612n51m2b 13 10 of of ADP 08612n51m2b 13 11 the the DET 08612n51m2b 13 12 ether ether NOUN 08612n51m2b 13 13 transfer transfer NOUN 08612n51m2b 13 14 methodology methodology NOUN 08612n51m2b 13 15 , , PUNCT 08612n51m2b 13 16 functionalization functionalization NOUN 08612n51m2b 13 17 , , PUNCT 08612n51m2b 13 18 and and CCONJ 08612n51m2b 13 19 radical radical ADJ 08612n51m2b 13 20 cyclization cyclization NOUN 08612n51m2b 13 21 to to PART 08612n51m2b 13 22 directly directly ADV 08612n51m2b 13 23 install install VERB 08612n51m2b 13 24 the the DET 08612n51m2b 13 25 requisite requisite ADJ 08612n51m2b 13 26 stereochemistry stereochemistry NOUN 08612n51m2b 13 27 embedded embed VERB 08612n51m2b 13 28 within within ADP 08612n51m2b 13 29 neopeltolide neopeltolide NOUN 08612n51m2b 13 30 's 's PART 08612n51m2b 13 31 tetrahydropyran tetrahydropyran NOUN 08612n51m2b 13 32 ring ring NOUN 08612n51m2b 13 33 . . PUNCT 08612n51m2b 14 1 our our PRON 08612n51m2b 14 2 synthesis synthesis NOUN 08612n51m2b 14 3 only only ADV 08612n51m2b 14 4 required require VERB 08612n51m2b 14 5 14 14 NUM 08612n51m2b 14 6 steps step NOUN 08612n51m2b 14 7 in in ADP 08612n51m2b 14 8 the the DET 08612n51m2b 14 9 longest long ADJ 08612n51m2b 14 10 linear linear ADJ 08612n51m2b 14 11 sequence sequence NOUN 08612n51m2b 14 12 , , PUNCT 08612n51m2b 14 13 15 15 NUM 08612n51m2b 14 14 steps step NOUN 08612n51m2b 14 15 overall overall ADV 08612n51m2b 14 16 . . PUNCT 08612n51m2b 15 1 more more ADV 08612n51m2b 15 2 importantly importantly ADV 08612n51m2b 15 3 , , PUNCT 08612n51m2b 15 4 it it PRON 08612n51m2b 15 5 was be AUX 08612n51m2b 15 6 free free ADJ 08612n51m2b 15 7 of of ADP 08612n51m2b 15 8 discreet discreet ADJ 08612n51m2b 15 9 installation installation NOUN 08612n51m2b 15 10 steps step NOUN 08612n51m2b 15 11 for for ADP 08612n51m2b 15 12 protecting protect VERB 08612n51m2b 15 13 groups group NOUN 08612n51m2b 15 14 , , PUNCT 08612n51m2b 15 15 thus thus ADV 08612n51m2b 15 16 representing represent VERB 08612n51m2b 15 17 a a DET 08612n51m2b 15 18 rare rare ADJ 08612n51m2b 15 19 example example NOUN 08612n51m2b 15 20 in in ADP 08612n51m2b 15 21 complex complex ADJ 08612n51m2b 15 22 polyketide polyketide NOUN 08612n51m2b 15 23 synthesis synthesis NOUN 08612n51m2b 15 24 . . PUNCT