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Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6‐Oxo‐isophorone: Syntheses of (3 R ,3′ R )‐Zeaxanthin. Part I
Author(s) -
Widmer Erich,
Soukup Milan,
Zell Reinhard,
Broger Emil,
Wagner Hans Peter,
Imfeld Marquard
Publication year - 1990
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.19900730411
Subject(s) - chemistry , isophorone , zeaxanthin , carotenoid , organic chemistry , combinatorial chemistry , stereochemistry , lutein , biochemistry , catalysis
Starting from the readily available, optically active (4 R )‐4‐hydroxy‐2,2,6‐trimethylcyclohexanone ( 1 ), a new technical synthesis of (3 R ,3′ R )‐zeaxanthin is described. According to a 2(C 9 + C 6 ) + C 10 = C 40 construction scheme, the ketone 1 was first transformed with ( E )‐3‐methylpent‐2‐en‐4‐yn‐1‐ol ( 5 ) into a C 15 ‐intermediate which, by a three‐step sequence, could be converted into the known olefinic C 15 ‐ Wittig salt 4 . Optimized conditions for the final Wittig reaction of 4 with the C 10 ‐dialdehyde 3 are discussed. Based on 1 , the overall yield of the entire technical process is ca. 40%.