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Synlett 1992; 1992(11): 875-877
DOI: 10.1055/s-1992-21524
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A Short Asymmetric Synthesis of (R,R)-(-)-Pyrenophorin

Jack E. Baldwin* , Robert M. Adlington, Steve H. Ramcharitar
  • *The Dyson Perrins Laboratory and the Oxford Centre for Molecular Sciences, University of Oxford, South Parks Road, Oxford OX1 3QY, England
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Publikationsdatum:
08. März 2002 (online)

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Palladium-catalysed cyclodimerisation of (R)-(-)-4-(tributylstannylpropenoate)-pentanoyl chloride 8 provided a facile and direct route to the antifungal macrodiolide (R,R)-(-)-Pyrenophorin 1 in 6 steps from the optically pure precursor (S)-(-)-γ-valerolactone. The optimal conditions used in the dimerisation reaction, a 4mM solution in toluene under 3 atmospheres of carbon monoxide at 100°C, afforded the title compound in 38% yield.