Studies towards the total synthesis of cycloaraneosene and ophiobolin M: A general strategy for the construction of the 5-8 bicyclic ring system

P K Ruprah, J P Cros, J E Pease, W G Whittingham, J M J Williams

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45 Citations (Scopus)

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. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Original languageEnglish
Pages (from-to)3145-3152
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number18
Publication statusPublished - 2002

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