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Allylic Sulfones Containing Triene Moieties as Key Synthons for Carotenoid Synthesis
Author(s) -
Ji Minkoo,
Choi Hojin,
Jeong Young Cheol,
Jin Jingquan,
Baik Woonphil,
Lee Sijoon,
Kim Jeong Soo,
Park Minsoo,
Koo Sangho
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390211
Subject(s) - sulfone , allylic rearrangement , chemistry , polyene , sulfide , synthon , moiety , sulfur , conjugated system , organic chemistry , catalysis , polymer
An efficient synthetic method for the allylic sulfone 2 containing a conjugated triene moiety has been proposed involving i ) coupling of allylic sulfones 4 with the C 5 bromoallylic sulfide 5 , ii ) base‐promoted dehydrosulfonation in the presence of allylic sulfide, and iii ) selective oxidation of the resulting trienyl sulfide to the corresponding sulfone. Total synthesis of lycopene starting from the C 15 allylic sulfone 2b has been described, where the new C 10 bis(chloroallylic) sulfone 11 proved to be a useful substitute for the C 10 bis(chloroallylic) sulfide 3 , which did not require the problematic chemoselective sulfur oxidation in a conjugated polyene.