An Efficient Approach to Chiral, Nonracemic trans-Decahydro-5,8a-dimethyl-1,6-naphthalenedione Derivatives: Total Synthesis of (+)-Pallescensin A

Article abstract of DOI:10.1021/jo00194a003

The syntheses of of six chiral, nonracemic trans-decahydro-5,8a-dimethyl-1,6-naphthalenedione derivatives 1a-f are described.The approach calls for the reductive alkylation of enone 4 readily available from (+)-Wieland-Miescher ketone (5) via chemoselective ketalization on the C(8)-carbonyl followed by application of the Kirk-Petrow (phenylthio)methylation protocol.Yields for reactive electrophiles are in the range of 70-85percent.To demonstrate the utility of this method, we record here a nine-step total synthesis of (+)-pallescensin A (8); the overall yield from enone 4 was 13percent.