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Synfacts 2020; 16(04): 0381
DOI: 10.1055/s-0039-1690086
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Saudin

Contributor(s):
Erick M. Carreira
,
Michael Schneider
Winkler JD. * Doherty EM. The University of Pennsylvania, Philadelphia, USA
The First Total Synthesis of (±)-Saudin.

J. Am. Chem. Soc. 1999;
121: 7425-7426
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Further Information

Publication History

Publication Date:
18 March 2020 (online)

 
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Key words

(±)-saudin - [2+2] cycloaddition - Stille cross-coupling - Michael addition–aldol addition cascade

Significance

Saudin is a diterpenoid that was isolated from Cluytia richardiana in 1985. It possesses a highly oxidized rearranged labdane skeleton and exhibits potent noninsulin dependent hypoglycemic activity. In 1999, Winkler and Doherty reported the first total synthesis of (±)-saudin by photochemical [2+2] cycloaddition of diene I.


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Comment

A Michael addition–aldol addition cascade of A and B afforded C. Irradiation of I gave cyclobutane J as a single diastereomer. The furyl substituent was introduced by ketene acetal triflate formation and Stille cross-coupling. The natural product was obtained by treating M first with aqueous base and then with acid.


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