原创力文档a practical chemo-enzymatic approach to highly enantio-enriched 10-ethyl-7,8-dihydro-γ-ionone isomers a method for the synthesis of 4,5-didehydro-α-ionone英文论文.pdfVIP
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a practical chemo-enzymatic approach to highly enantio-enriched 10-ethyl-7,8-dihydro-γ-ionone isomers a method for the synthesis of 4,5-didehydro-α-ionone英文论文
Int. J. Mol. Sci. 2012, 13, 5542-5553; doi:10.3390/ijm
OPEN ACCESS
International Journal of
Molecular Sciences
ISSN 1422-0067
/journal/ijms
Article
A Practical Chemo-enzymatic Approach to Highly
Enantio-Enriched 10-Ethyl-7,8-dihydro-γ-ionone Isomers:
A Method for the Synthesis of 4,5-Didehydro-α-Ionone
Assem Barakat *, Abdullah M. Al-Majid, Yahia Nasser Mabkhot and Zeid Abdullah Al-Othman
Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451,
Saudi Arabia; E-Mails: amajid@.sa (A.M.A.-M.); yahia@.sa (Y.N.M.);
zaothman@.sa (Z.A.A.-O.)
* Author to whom correspondence should be addressed; E-Mail: ambarakat@.sa;
Tel.: +96-614-675-884; Fax: +96-614-675-992.
Received: 15 March 2012; in revised form: 23 April 2012 / Accepted: 2 May 2012 /
Published: 9 May 2012
Abstract: An efficient and convenient strategy for the enantioselective synthesis of
enantiomerically enriched 10-ethyl-7,8-dihydro-γ-ionone isomers (R)-(+)-7, and (S)-(−)-7
are described utilizing a lipase mediated resolution protocol, and reductive elimination of
the secondary allylic alcohol as the key step. The enantioselective and diastereoselective
lipase kinetic acetylation of 4-hydroxy-γ-ionone derivatives 6a afforded the
4-acetyl-γ-ionone derivatives (−)-8, and the 4-hydrox-γ-ionone derivatives (+)-6a, which
are suitable precursors of the desired products. Stereospecific palladium-mediated
elimination of
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