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Synfacts 2010(4): 0376-0376  
DOI: 10.1055/s-0029-1219451
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Syntheses of (+)-Echinopine A and B

Contributor(s): Steven V. Ley, David J. France
T. Magauer*, J. Mulzer, K. Tiefenbacher*
University of Vienna, Austria
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

The first synthesis of echinopines A and B features a [3,3]-sigmatropic rearrangement developed by A. G. Myers et al. (Tetrahedron Lett. 1996, 37, 4841) to install the vinyl group at C1 on the concave face of bicyclo[3.3.0]octane C. Closure of 5,5,7-tricycle F occurs by ring-closing metathesis. Two-carbon homologation using a ­silyl ketene acetal gives ­ester G.