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Synlett 1992; 1992(11): 875-877
DOI: 10.1055/s-1992-21524
DOI: 10.1055/s-1992-21524
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved.
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data processing and storage.A Short Asymmetric Synthesis of (R,R)-(-)-Pyrenophorin
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Publikationsverlauf
Publikationsdatum:
08. März 2002 (online)

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.