Journal of Organic Chemistry p. 3685 - 3689 (1984)
Update date:2022-08-03
Topics:
Smith, Amos B.
Mewshaw, Richard
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.
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