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. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
|Number of pages||8|
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - 2002|