Abstract
The application of Michael addition to the construction of the carbon skeleton of 9,11-secosterols has been investigated using the following Michael acceptor - sulfone 2-[(4-methylphenyl)sulfonyl]cyclopent-2-en-1-one, where the addition product was isolated in good yield and as a mixture of two diastereomers. Also, the diastereomers were separable by crystallization, and, based on NMR spectroscopic data, the relative configuration of the formed stereocentres of the isolated diastereomer matched the 9,11-secosterol found in nature. This study can be exploited to create a total synthesis scheme for 9,11-secosterols.
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