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A Highly Efficient Chain‐Extension Process in the Systematic Syntheses of Carotenoid Natural Products
Author(s) -
Ji Minkoo,
Choi Hojin,
Park Minsoo,
Kee Minyong,
Jeong Young Cheol,
Koo Sangho
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20011001)40:19<3627::aid-anie3627>3.0.co;2-e
Subject(s) - carotenoid , allylic rearrangement , sulfone , sulfide , chain (unit) , work (physics) , unit (ring theory) , chemistry , process (computing) , coupling (piping) , extension (predicate logic) , organic chemistry , mathematics , computer science , materials science , engineering , physics , catalysis , composite material , mathematics education , programming language , food science , astronomy , operating system , mechanical engineering
Successive elongation by a C 5 unit is possible when an allylic sulfone is coupled with 4‐bromo‐3‐methyl‐2‐butenyl phenyl sulfide ( 1 ). The thiosulfone compound formed was then oxidized to the corresponding disulfone, which, upon coupling with another equivalent of 1 and oxidation, produced the trisulfone 2 , again elongated by a C 5 unit (see scheme). This process, which can be repeated again, is the basis for a highly efficient synthesis of carotenoids.