Application of Intramolecular Enyne Metathesis to the Synthesis of Aza[4.2.1]bicyclics:  Enantiospecific Total Synthesis of (+)-Anatoxin-a

Jehrod B. Brenneman and Stephen F. Martin*
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712
Org. Lett., 2004, 6 (8), pp 1329–1331
DOI: 10.1021/ol049631e
Publication Date (Web): March 23, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sfmartin@mail.utexas.edu

Abstract

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A concise synthesis of the potent nAChR agonist (+)-anatoxin-a (1) has been completed in a series of only nine chemical operations and 27% overall yield from commercially available d-methyl pyroglutamate (4). The synthesis features a novel procedure for the diastereoselective preparation of cis-2,5-disubstituted pyrrolidines leading to 10, which underwent an intramolecular enyne metathesis to afford a bridged azabicyclic intermediate that was transformed into 1.

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History

  • Published In Issue April 15, 2004
  • Received February 29, 2004

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