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A new strategy for the synthesis of (+)-vernolepin related compounds: an unusual sulfene elimination leads to the 2-oxa-cis-decalin skeleton

✍ Scribed by Alejandro F Barrero; J.Enrique Oltra; Mı́riam Álvarez

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 102 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01334-4

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✦ Synopsis

A new strategy for the synthesis of (+)-vernolepin (1), (+)-vernodalin (2), and (+)-8-deoxyvernolepin (3), from the accessible germacrolides (+)-salonitenolide ( 4) and (+)-costunolide (5), has been developed. The key steps in the synthesis are a Cope rearrangement from the germacradiene to the elemadiene skeleton, the cyclization of a trans-fused d-lactone from an epoxy ester, and an unusual sulfene elimination, which promotes a reaction cascade leading to the 2-oxa-cis-decalin skeleton.

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