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ChemInform Abstract: Type II Intramolecular Annulations Between Vinylcarbenoids and Furans.

✍ Scribed by H. M. L. DAVIES; R. CALVO; G. AHMED

Publisher: John Wiley and Sons
Year: 2010
Weight: 29 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199726048

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✦ Synopsis

Type II Intramolecular Annulations Between Vinylcarbenoids and Furans.

-Model studies for the synthesis of (4.3.1)-bicyclic frameworks containing an anti-Bredt double bond recently found in new squalene synthetase inhibiting terpenes are reported. Thus, Cope-rearrangement of cyclopropane (IV) unexpectedly gives the fused cyclobutane (V), probably via the desired (4.3.1)-bicycle as intermediate. Similar treatment of the furans (VI) provides a tandem cyclopropanation/Cope rearrangement to the desired fused (4.3.1)bicyclic systems (VII). -(DAVIES, H.

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