A New Total Synthesis of (+)-Brefeldin C

Abstract

A new synthesis of (+)-brefeldin C featuring a Bolm desymmetrisation reaction, a B-alkyl Suzuki-Miyaura cross-coupling and a Carreira alkynylation reaction as the key steps is reported.

Key words

brefeldin C - Bolm desymmetrisation reaction - B-alkyl Suzuki-Miyaura cross-coupling - Carreira alkynylation reaction - ­total synthesis

References

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12

Alcool 15a was separated from its minor diastereoisomer 15b by column chromatography on silica (eluent: petroleum ether-EtOAc, 4:1). At this stage, the absolute configuration at C4 was tentatively assigned on the basis of precedent⁷ and was confirmed later by the obtention of (+)-BFC.

14

We thank Pr. M. Evain (Institut des Matériaux Jean Rouxel, Nantes) for X-ray analysis.