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Studies on the synthesis of ginkgolides rapid construction of the spiro 4.4 nonane a and b rings

, : Studies on the synthesis of ginkgolides rapid construction of the spiro 4.4 nonane a and b rings. Journal of the Chemical Society Perkin Transactions I (11): 2661-2668

The functionalised spiro[4.4]nonane 30 is available from tert-butylcyclopentadiene 16 via spiroalkylation with 12b to give 17/18, followed by singlet oxygenation/aldolisation to the mixture of 21, 22, 25 and 26. Oxidation of the mixture gave two enediones 28/29, which were reduced with K-Selectride and the diastereoisomer 26 was separated and hydrogenated to give 30.


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