An Efficient Synthesis of 7-endo-t-Butyldimethylsilyloxy-bicyclo[3.3.0]oct-8-en-2-one

References

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• The purification of the silyl ether (4) is essential because the hydrogenolysis without purification afforded the diol (11) as the major product.
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• Based on the TLC analysis, a trace amount of the diol (11) was observed
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• The hydroxy-enone (10) was obtained as follows: The exo-epoxide (12), which was stereoselectively synthesized from 1 by treatment with m-chloroperbenzoic acid in t-butyl alcohol2,3 (exo:endo = 9:1), was oxidized with PCC to afford the ketone (13). Then, the ketone (13) was reacted with sodium carbonate in t-butyl alcohol-water (1:3) at room temperature for 15 min to give the enone (10)(νCHCl max3 1720, 1640 cm-1, δCDCl TMS3 6.54 (1H, triplet, J=3 Hz), m/e 138 [M+]) in 10% overall yield
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