ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Syntheses of Enantiomerically Pure Violaxanthins and Related CompoundsThe epoxides 16 and ent-16, prepared by Sharpless-Katsuki oxidation of 15 in excellent yield and very high enantiomeric purity, were used as synthons for the preparation of (+)-(S)-didehydrovomifoliol (45), (+)-(6S, 7E, 9E)-abscisic ester 46, (+)-(6S, 7E, 9Z)-abscsic ester 47, (-)-(3S, 7E, 9E)-xanthoxin (49), (-)-(3R, 7E, 9E)-xanthoxin (50), (3S, 5R, 6S, 3′S,5′R, 6′S, all-E)-violaxanthin (1) (3R, 5R,6S,3′R,5′R,6′S, all-E)-violaxanthin (55) and their (9Z) (see 53, 57), (13Z) (see 54, 58), and (15Z) (see 60) isomers. The novel violadione (61) was prepared from 1 by oxidation with DMSO/Ac2O. By base treatment, 61 was converted into violadienedione (62), a potential precursor of carotenoids with phenolic end groups.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19880710502
