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Org Lett. 2007 Dec 20;9(26):5533-6. Epub 2007 Nov 21.

Synthetic study of diversifolin: the construction of 11-oxabicyclo[6.2.1]undec-3-ene core using ring-closing metathesis.

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  • 1Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.

Abstract

Stereoselective synthesis of a potential intermediate bearing 11-oxabicyclo[6.2.1]undec-3-ene core, a common scaffold of biologically active germacrane-type sesquiterpenes, has been achieved. Synthetic features involve formal 1,3-asymmetric induction, unusual ring-closing metathesis constructing a 10-membered carbocycle system, and unique lactone transposition.

PMID:
18027960
DOI:
10.1021/ol7025119
[PubMed - indexed for MEDLINE]
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