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Synfacts 2006(2): 0097-0097
DOI: 10.1055/s-2005-923601
DOI: 10.1055/s-2005-923601
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of (-)-Spirotryprostatin B
C. Marti, E. M. Carreira*
ETH Hoenggerberg, Zürich, Switzerland
Further Information
Publication History
Publication Date:
23 January 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200602/lookinside/thumbnails/10.1055-s-2005-923601-1.jpg)
Significance
The salient feature of the Carreira synthesis of (-)-Spirotryprostatin B is a MgI2-mediated ring-expansion reaction via putative intermediate D to construct the spiro[pyrrolidine-3,3′-oxindole] core. The Carreira group has also applied the MgI2-mediated ring expansion to the synthesis of Horsifiline (C. Fischer, C. Meyers, E. M. Carreira Helv. Chim. Acta 2000, 83, 1175-1181) and Strychnofoline (A. Lerchner, E. M. Carreira J. Am. Chem. Soc. 2002, 124, 14826-14827).