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Synfacts 2007(8): 0792-0792  
DOI: 10.1055/s-2007-968708
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Attenol B

Contributor(s): Philip Kocienski
T. E. La Cruz, S. D. Rychnovsky*
University of California, Irvine, USA
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

In contrast to traditional spiroacetal syntheses, Rychnovsky’s reductive cyclization approach (S. D. Rychnovsky and co-workers J. Am. Chem. Soc. 2005, 127, 528) gives rise to a spiro­acetal which is not the thermodynamic product. In the case of attenol A, the generation of organolithium G by reductive cleavage of the cyanoacetal F and its cyclization to H were highly stereoselective.