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Letter

Total Synthesis of (+)-Cocaine via Desymmetrization of a meso-Dialdehyde

Supporting Info

Douglas M. Mans and William H. Pearson*^†

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055

Org. Lett., 2004, 6 (19), pp 3305–3308

DOI: 10.1021/ol048777a

Publication Date (Web): August 19, 2004

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

†

Current Address: Berry and Associates, Inc., 2434 Bishop Circle East, Dexter, MI 48130.

, wpearson@berryassoc.com

Abstract

The total synthesis of (+)-cocaine is described. An extension of the recently reported proline catalyzed intramolecular enol−exo-aldol reaction to a meso-dialdehyde provided the tropane ring skeleton directly with good enantiomeric excess. The meso-dialdehyde was prepared using a 2-azaallyllithium [3 + 2] cycloaddition to generate a cis-2,5-disubstituted pyrrolidine. Overall, the synthesis proceeded in 6.5% yield and 86% ee over 14 linear steps starting from commercially available 3-benzyloxy-1-propanol.

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Published In Issue September 16, 2004
Received June 27, 2004

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Letter

Total Synthesis of (+)-Cocaine via Desymmetrization of a meso-Dialdehyde

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

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

Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d- and l-Glutamic Acid

Enantiospecific Total Syntheses of Kapakahines B and F

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