Abstract
The synthesis of the core unit of cycloaraneosene and ophiobolin M has been investigated, following a general strategy applicable to both 5−8 bicyclic systems. The synthetic strategy includes a ring-closing metathesis reaction to generate the central eight-membered ring as well as a palladium-mediated coupling of a Grignard reagent to introduce the exocyclic side-chain. The stereochemistry of the ring junction is also discussed and moderate diastereoselectivity has been achieved. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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