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Synthesis of Bixin and Three Minor Carotenoids from Annatto ( Bixa orellana )
Author(s) -
Häberli Adrian,
Pfander Hanspeter
Publication year - 1999
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/(sici)1522-2675(19990505)82:5<696::aid-hlca696>3.0.co;2-x
Subject(s) - polyene , chemistry , wittig reaction , phosphonium , organic chemistry , stereochemistry
The three apocarotenoids methyl (9 Z )‐8′‐oxo‐6,8′‐diapocaroten‐6‐oate ( 2 ), methyl (9 Z )‐10′‐oxo‐6,10′‐diapocaroten‐6‐oate ( 4 ), and methyl (9 Z )‐14′‐oxo‐6,14′‐diapocaroten‐6‐oate ( 5 ), recently isolated from annatto, were synthesized. The key step of all three syntheses was the Wittig reaction of the ( Z )‐terminus 6 with the phosphonium salts 15 , 18 , and 24 , carrying the polyene chain. Bixin ( 1 ) was synthesized from 2 in a Horner‐Emmons reaction.