23068-96-4Relevant articles and documents
Lipase-mediated resolution of the hydroxy-cyclogeraniol isomers: application to the synthesis of the enantiomers of karahana lactone, karahana ether, crocusatin C and γ-cyclogeraniol
Serra, Stefano,Gatti, Francesco G.,Fuganti, Claudio
experimental part, p. 1319 - 1329 (2009/12/01)
A comprehensive study on the lipase PS-mediated resolution of different hydroxy-geraniol isomers is reported. A number of α-, β- and γ-isomers bearing a 2-, 3- or 4-hydroxy functional group were synthesised regioselectively and then submitted to the lipase-mediated kinetic acetylation. The latter experiments showed that the 2-hydroxy isomers 4, 5 and 14 (α, γ and β, respectively) as well as cis-3-hydroxy α-cyclogeraniol 7 and cis-4-hydroxy γ-cyclogeraniol 10 could be easily resolved by this procedure. The enantiomeric purity of the main part of these compounds was increased by recrystallisation and the enantiopure diols obtained were used as building blocks for the synthesis of the natural terpenoids karahana lactone, karahana ether and crocusatin C and for the preparation of the synthetic intermediate γ-cyclogeraniol. The absolute configurations of the enantiomers of the diols 7, 10, 14 and 19 were determined by chemical correlation with the known compounds 40, 41, 39 and 41, respectively.
Syntheses of Enantiomerically Pure Violaxanthins and Related Compounds
Acemoglu, Murat,Uebelhart, Peter,Rey, Max,Eugster, Conrad Hans
, p. 931 - 956 (2007/10/02)
The 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)-abscisic 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.
A new Convenient Synthesis of 3-Hydroxy-β-damascone
Tsujino, Yasuko,Shibagaki, Makoto,Matsushita, Hajime,Kato, Kunio,Kaneko, Hajime
, p. 1731 - 1732 (2007/10/02)
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