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Technische Verfahren zur Synthese von Carotinoiden und verwandten Verbindungen aus 6‐Oxo‐isophoron. II. Ein neues Konzept für die Synthese von (3 RS , 3′ RS )‐Astaxanthin
Author(s) -
Widmer Erich,
Zell Reinhard,
Broger Emil Albin,
Crameri Yvo,
Wagner Hans Peter,
Dinkel Josef,
Schlageter Markus,
Lukáč T+odor
Publication year - 1981
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.19810640751
Subject(s) - chemistry , astaxanthin , isophorone , total synthesis , stereochemistry , carotenoid , organic chemistry , biochemistry , catalysis
Technical Procedures for the Synthesis of Carotenoids and Related Compounds from 6‐Oxo‐isophorone. II. A Novel Concept for the Synthesis of (3 RS , 3′ RS )‐Astaxanthin Starting from 6‐oxo‐isophorone ( 2 ) a new concept for a seven‐step synthesis of (3 RS , 3′ RS )‐astaxanthin ( 1 ) has been developed. As a key feature of the new approach, the oxidation state of astaxanthin ( 1 ) is adjusted already at an early stage of the synthesis. Thus, manipulation on more complex intermediates later in the synthesis is reduced to a minimum. Acetonide 10 or dimer 13 represent the key intermediates of this concept (Scheme 2) . The whole sequence has been run on a kg scale with an overall yield of 52% (s. Scheme 5 ).