id sid tid token lemma pos tb09j388f51 1 1 this this DET tb09j388f51 1 2 dissertation dissertation NOUN tb09j388f51 1 3 comprises comprise VERB tb09j388f51 1 4 three three NUM tb09j388f51 1 5 major major ADJ tb09j388f51 1 6 components component NOUN tb09j388f51 1 7 that that PRON tb09j388f51 1 8 sequentially sequentially ADV tb09j388f51 1 9 describe describe VERB tb09j388f51 1 10 the the DET tb09j388f51 1 11 development development NOUN tb09j388f51 1 12 of of ADP tb09j388f51 1 13 three three NUM tb09j388f51 1 14 methodologies methodology NOUN tb09j388f51 1 15 for for ADP tb09j388f51 1 16 the the DET tb09j388f51 1 17 formation formation NOUN tb09j388f51 1 18 of of ADP tb09j388f51 1 19 novel novel ADJ tb09j388f51 1 20 methyl methyl NOUN tb09j388f51 1 21 substituted substitute VERB tb09j388f51 1 22 polyketide polyketide PROPN tb09j388f51 1 23 structural structural ADJ tb09j388f51 1 24 units unit NOUN tb09j388f51 1 25 and and CCONJ tb09j388f51 1 26 their their PRON tb09j388f51 1 27 application application NOUN tb09j388f51 1 28 in in ADP tb09j388f51 1 29 complex complex ADJ tb09j388f51 1 30 molecule molecule NOUN tb09j388f51 1 31 synthesis synthesis NOUN tb09j388f51 1 32 . . PUNCT tb09j388f51 2 1 this this DET tb09j388f51 2 2 research research NOUN tb09j388f51 2 3 dissertation dissertation NOUN tb09j388f51 2 4 commences commence VERB tb09j388f51 2 5 with with ADP tb09j388f51 2 6 a a DET tb09j388f51 2 7 literature literature NOUN tb09j388f51 2 8 review review NOUN tb09j388f51 2 9 pertinent pertinent ADJ tb09j388f51 2 10 to to ADP tb09j388f51 2 11 the the DET tb09j388f51 2 12 development development NOUN tb09j388f51 2 13 of of ADP tb09j388f51 2 14 an an DET tb09j388f51 2 15 ether ether NOUN tb09j388f51 2 16 transfer transfer NOUN tb09j388f51 2 17 protocol protocol NOUN tb09j388f51 2 18 , , PUNCT tb09j388f51 2 19 enabling enable VERB tb09j388f51 2 20 a a DET tb09j388f51 2 21 novel novel ADJ tb09j388f51 2 22 access access NOUN tb09j388f51 2 23 to to ADP tb09j388f51 2 24 the the DET tb09j388f51 2 25 formation formation NOUN tb09j388f51 2 26 of of ADP tb09j388f51 2 27 1,3 1,3 PROPN tb09j388f51 2 28 - - PUNCT tb09j388f51 2 29 syn syn NOUN tb09j388f51 2 30 - - PUNCT tb09j388f51 2 31 diol diol NOUN tb09j388f51 2 32 monoor monoor ADJ tb09j388f51 2 33 diethers diether NOUN tb09j388f51 2 34 through through ADP tb09j388f51 2 35 electrophilic electrophilic ADJ tb09j388f51 2 36 activation activation NOUN tb09j388f51 2 37 of of ADP tb09j388f51 2 38 homoallylic homoallylic ADJ tb09j388f51 2 39 alkoxymethyl alkoxymethyl NOUN tb09j388f51 2 40 ethers ether NOUN tb09j388f51 2 41 . . PUNCT tb09j388f51 3 1 starting start VERB tb09j388f51 3 2 from from ADP tb09j388f51 3 3 1,1 1,1 PROPN tb09j388f51 3 4 - - PUNCT tb09j388f51 3 5 disubstituted disubstitute VERB tb09j388f51 3 6 alkenes alkene NOUN tb09j388f51 3 7 , , PUNCT tb09j388f51 3 8 this this DET tb09j388f51 3 9 transformation transformation NOUN tb09j388f51 3 10 enabled enable VERB tb09j388f51 3 11 us we PRON tb09j388f51 3 12 to to PART tb09j388f51 3 13 stereoselectively stereoselectively ADV tb09j388f51 3 14 access access VERB tb09j388f51 3 15 tertiary tertiary ADJ tb09j388f51 3 16 ethers ether NOUN tb09j388f51 3 17 . . PUNCT tb09j388f51 4 1 the the DET tb09j388f51 4 2 use use NOUN tb09j388f51 4 3 of of ADP tb09j388f51 4 4 iodine iodine NOUN tb09j388f51 4 5 monochloride monochloride PROPN tb09j388f51 4 6 proved prove VERB tb09j388f51 4 7 critical critical ADJ tb09j388f51 4 8 for for ADP tb09j388f51 4 9 a a DET tb09j388f51 4 10 selective selective ADJ tb09j388f51 4 11 process process NOUN tb09j388f51 4 12 , , PUNCT tb09j388f51 4 13 but but CCONJ tb09j388f51 4 14 other other ADJ tb09j388f51 4 15 reagents reagent NOUN tb09j388f51 4 16 such such ADJ tb09j388f51 4 17 as as ADP tb09j388f51 4 18 idsi idsi PROPN tb09j388f51 4 19 and and CCONJ tb09j388f51 4 20 bdsb bdsb NOUN tb09j388f51 4 21 have have AUX tb09j388f51 4 22 shown show VERB tb09j388f51 4 23 to to PART tb09j388f51 4 24 be be AUX tb09j388f51 4 25 as as ADV tb09j388f51 4 26 efficient efficient ADJ tb09j388f51 4 27 . . PUNCT tb09j388f51 5 1 additional additional ADJ tb09j388f51 5 2 advancements advancement NOUN tb09j388f51 5 3 have have AUX tb09j388f51 5 4 led lead VERB tb09j388f51 5 5 to to ADP tb09j388f51 5 6 the the DET tb09j388f51 5 7 discovery discovery NOUN tb09j388f51 5 8 of of ADP tb09j388f51 5 9 2 2 NUM tb09j388f51 5 10 - - PUNCT tb09j388f51 5 11 naphthylmethyl naphthylmethyl NOUN tb09j388f51 5 12 ether ether NOUN tb09j388f51 5 13 which which PRON tb09j388f51 5 14 proceeded proceed VERB tb09j388f51 5 15 smoothly smoothly ADV tb09j388f51 5 16 through through ADP tb09j388f51 5 17 ether ether NOUN tb09j388f51 5 18 transfer transfer NOUN tb09j388f51 5 19 and and CCONJ tb09j388f51 5 20 was be AUX tb09j388f51 5 21 easily easily ADV tb09j388f51 5 22 cleaved cleave VERB tb09j388f51 5 23 by by ADP tb09j388f51 5 24 ddq ddq PROPN tb09j388f51 5 25 oxidation oxidation NOUN tb09j388f51 5 26 . . PUNCT tb09j388f51 6 1 this this DET tb09j388f51 6 2 new new ADJ tb09j388f51 6 3 method method NOUN tb09j388f51 6 4 to to PART tb09j388f51 6 5 access access VERB tb09j388f51 6 6 structural structural ADJ tb09j388f51 6 7 units unit NOUN tb09j388f51 6 8 containing contain VERB tb09j388f51 6 9 tertiary tertiary ADJ tb09j388f51 6 10 ethers ether NOUN tb09j388f51 6 11 was be AUX tb09j388f51 6 12 applied apply VERB tb09j388f51 6 13 in in ADP tb09j388f51 6 14 the the DET tb09j388f51 6 15 synthesis synthesis NOUN tb09j388f51 6 16 of of ADP tb09j388f51 6 17 the the DET tb09j388f51 6 18 c9 c9 NOUN tb09j388f51 6 19 - - PUNCT tb09j388f51 6 20 c19 c19 NOUN tb09j388f51 6 21 fragment fragment NOUN tb09j388f51 6 22 of of ADP tb09j388f51 6 23 lyngbyaloside lyngbyaloside PROPN tb09j388f51 6 24 b b PROPN tb09j388f51 6 25 and and CCONJ tb09j388f51 6 26 c. c. PROPN tb09j388f51 6 27 in in ADP tb09j388f51 6 28 several several ADJ tb09j388f51 6 29 cases case NOUN tb09j388f51 6 30 , , PUNCT tb09j388f51 6 31 we we PRON tb09j388f51 6 32 observed observe VERB tb09j388f51 6 33 the the DET tb09j388f51 6 34 failure failure NOUN tb09j388f51 6 35 of of ADP tb09j388f51 6 36 the the DET tb09j388f51 6 37 ether ether NOUN tb09j388f51 6 38 transfer transfer NOUN tb09j388f51 6 39 methodology methodology NOUN tb09j388f51 6 40 to to PART tb09j388f51 6 41 provide provide VERB tb09j388f51 6 42 the the DET tb09j388f51 6 43 desired desire VERB tb09j388f51 6 44 reactivity reactivity NOUN tb09j388f51 6 45 . . PUNCT tb09j388f51 7 1 this this PRON tb09j388f51 7 2 was be AUX tb09j388f51 7 3 particularly particularly ADV tb09j388f51 7 4 true true ADJ tb09j388f51 7 5 when when SCONJ tb09j388f51 7 6 sp2 sp2 NOUN tb09j388f51 7 7 - - PUNCT tb09j388f51 7 8 hybridized hybridize VERB tb09j388f51 7 9 substituents substituent NOUN tb09j388f51 7 10 were be AUX tb09j388f51 7 11 adjacent adjacent ADJ tb09j388f51 7 12 to to ADP tb09j388f51 7 13 the the DET tb09j388f51 7 14 reacting react VERB tb09j388f51 7 15 alkoxymethyl alkoxymethyl NOUN tb09j388f51 7 16 ether ether NOUN tb09j388f51 7 17 , , PUNCT tb09j388f51 7 18 resulting result VERB tb09j388f51 7 19 in in ADP tb09j388f51 7 20 the the DET tb09j388f51 7 21 formation formation NOUN tb09j388f51 7 22 of of ADP tb09j388f51 7 23 dihalogenated dihalogenated ADJ tb09j388f51 7 24 byproducts byproduct NOUN tb09j388f51 7 25 upon upon SCONJ tb09j388f51 7 26 activation activation NOUN tb09j388f51 7 27 with with ADP tb09j388f51 7 28 iodine iodine NOUN tb09j388f51 7 29 monochloride monochloride PROPN tb09j388f51 7 30 . . PUNCT tb09j388f51 8 1 we we PRON tb09j388f51 8 2 therefore therefore ADV tb09j388f51 8 3 developed develop VERB tb09j388f51 8 4 a a DET tb09j388f51 8 5 second second ADJ tb09j388f51 8 6 generation generation NOUN tb09j388f51 8 7 of of ADP tb09j388f51 8 8 activating activate VERB tb09j388f51 8 9 conditions condition NOUN tb09j388f51 8 10 , , PUNCT tb09j388f51 8 11 using use VERB tb09j388f51 8 12 n n NOUN tb09j388f51 8 13 - - PUNCT tb09j388f51 8 14 iodosuccinimide iodosuccinimide NOUN tb09j388f51 8 15 in in ADP tb09j388f51 8 16 wet wet ADJ tb09j388f51 8 17 nitromethane nitromethane NOUN tb09j388f51 8 18 , , PUNCT tb09j388f51 8 19 to to PART tb09j388f51 8 20 resolve resolve VERB tb09j388f51 8 21 this this DET tb09j388f51 8 22 lack lack NOUN tb09j388f51 8 23 of of ADP tb09j388f51 8 24 selectivity selectivity NOUN tb09j388f51 8 25 . . PUNCT tb09j388f51 9 1 this this DET tb09j388f51 9 2 new new ADJ tb09j388f51 9 3 , , PUNCT tb09j388f51 9 4 stereoselective stereoselective ADJ tb09j388f51 9 5 route route NOUN tb09j388f51 9 6 to to PART tb09j388f51 9 7 access access VERB tb09j388f51 9 8 1,3 1,3 NUM tb09j388f51 9 9 - - PUNCT tb09j388f51 9 10 syn syn NOUN tb09j388f51 9 11 - - PUNCT tb09j388f51 9 12 diol diol NOUN tb09j388f51 9 13 monoor monoor ADJ tb09j388f51 9 14 diethers diether NOUN tb09j388f51 9 15 was be AUX tb09j388f51 9 16 successfully successfully ADV tb09j388f51 9 17 applied apply VERB tb09j388f51 9 18 to to ADP tb09j388f51 9 19 the the DET tb09j388f51 9 20 syntheses synthesis NOUN tb09j388f51 9 21 of of ADP tb09j388f51 9 22 diospongins diospongin NOUN tb09j388f51 9 23 a a PRON tb09j388f51 9 24 and and CCONJ tb09j388f51 9 25 b. b. PROPN tb09j388f51 9 26 the the DET tb09j388f51 9 27 final final ADJ tb09j388f51 9 28 section section NOUN tb09j388f51 9 29 describes describe VERB tb09j388f51 9 30 a a DET tb09j388f51 9 31 method method NOUN tb09j388f51 9 32 that that PRON tb09j388f51 9 33 enabled enable VERB tb09j388f51 9 34 sp3 sp3 DET tb09j388f51 9 35 c c NOUN tb09j388f51 9 36 - - PUNCT tb09j388f51 9 37 h h NOUN tb09j388f51 9 38 bond bond NOUN tb09j388f51 9 39 functionalization functionalization NOUN tb09j388f51 9 40 by by ADP tb09j388f51 9 41 means mean NOUN tb09j388f51 9 42 of of ADP tb09j388f51 9 43 a a DET tb09j388f51 9 44 hydride hydride NOUN tb09j388f51 9 45 shift shift NOUN tb09j388f51 9 46 . . PUNCT tb09j388f51 10 1 we we PRON tb09j388f51 10 2 discovered discover VERB tb09j388f51 10 3 that that SCONJ tb09j388f51 10 4 protonation protonation NOUN tb09j388f51 10 5 of of ADP tb09j388f51 10 6 an an DET tb09j388f51 10 7 alkene alkene NOUN tb09j388f51 10 8 with with ADP tb09j388f51 10 9 a a DET tb09j388f51 10 10 strong strong ADJ tb09j388f51 10 11 br?nsted br?nsted ADJ tb09j388f51 10 12 acid acid NOUN tb09j388f51 10 13 initiated initiate VERB tb09j388f51 10 14 a a DET tb09j388f51 10 15 1,5 1,5 NUM tb09j388f51 10 16 - - PUNCT tb09j388f51 10 17 hydride hydride NOUN tb09j388f51 10 18 shift shift NOUN tb09j388f51 10 19 through through ADP tb09j388f51 10 20 reduction reduction NOUN tb09j388f51 10 21 of of ADP tb09j388f51 10 22 a a DET tb09j388f51 10 23 tertiary tertiary ADJ tb09j388f51 10 24 carbocation carbocation NOUN tb09j388f51 10 25 by by ADP tb09j388f51 10 26 an an DET tb09j388f51 10 27 appropriately appropriately ADV tb09j388f51 10 28 positioned position VERB tb09j388f51 10 29 benzyl benzyl NOUN tb09j388f51 10 30 ether ether NOUN tb09j388f51 10 31 . . PUNCT tb09j388f51 11 1 modifications modification NOUN tb09j388f51 11 2 to to ADP tb09j388f51 11 3 the the DET tb09j388f51 11 4 starting starting NOUN tb09j388f51 11 5 material material NOUN tb09j388f51 11 6 or or CCONJ tb09j388f51 11 7 to to ADP tb09j388f51 11 8 the the DET tb09j388f51 11 9 activating activating NOUN tb09j388f51 11 10 conditions condition NOUN tb09j388f51 11 11 allowed allow VERB tb09j388f51 11 12 the the DET tb09j388f51 11 13 formation formation NOUN tb09j388f51 11 14 of of ADP tb09j388f51 11 15 a a DET tb09j388f51 11 16 variety variety NOUN tb09j388f51 11 17 of of ADP tb09j388f51 11 18 synthetically synthetically ADV tb09j388f51 11 19 useful useful ADJ tb09j388f51 11 20 motifs motif NOUN tb09j388f51 11 21 that that PRON tb09j388f51 11 22 could could AUX tb09j388f51 11 23 be be AUX tb09j388f51 11 24 potentially potentially ADV tb09j388f51 11 25 employed employ VERB tb09j388f51 11 26 in in ADP tb09j388f51 11 27 the the DET tb09j388f51 11 28 synthesis synthesis NOUN tb09j388f51 11 29 of of ADP tb09j388f51 11 30 complex complex ADJ tb09j388f51 11 31 natural natural ADJ tb09j388f51 11 32 products product NOUN tb09j388f51 11 33 . . PUNCT