Concepedia

A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids

Alexander F. G. Goldberg, Brian M. Stoltz

Organic Letters · 2011 · 117 citations · 16 references

DOI

Concepts

Abstract

A palladium-catalyzed (3+2) cycloaddition of a vinylcyclopropane and a β-nitrostyrene is employed to rapidly assemble the cyclopentane core of the Melodinus alkaloids. The ABCD ring system of the natural product family is prepared in six steps from commercially available materials.

References

16

Palladium‐Catalyzed Diastereo‐ and Enantioselective Synthesis of Substituted Cyclopentanes through a Dynamic Kinetic Asymmetric Formal [3+2]‐Cycloaddition of Vinyl Cyclopropanes and Alkylidene Azlactones

Barry M. Trost, Patrick J. Morris · Angewandte Chemie International Edition · 2011 · 228 citations

, , +7

Palladium-catalyzed [3 + 2] cycloaddition reaction of vinylcyclopropanes with α,β-unsaturated esters or ketones

Isao Shimizu, Yukihiro Ohashi, Jiro Tsuji · Tetrahedron Letters · 1985 · 175 citations

, , +6

Diastereoselective Synthesis of Tetrahydrofurans via Palladium(0)-Catalyzed [3 + 2] Cycloaddition of Vinylcyclopropanes and Aldehydes

Andrew T. Parsons, Matthew Campbell, Jeffrey S. Johnson · Organic Letters · 2008 · 166 citations

, , +13

Use of aza-Cope rearrangement-Mannich cyclization reactions to achieve a general entry to Melodinus and Aspidosperma alkaloids. Stereocontrolled total syntheses of (.+-.)-deoxoapodine, (.+-.)-meloscine, and (.+-.)-epimeloscine and a formal synthesis of (.+-.)-1-acetylaspidoalbidine

Larry E. Overman, G.M. Robertson, Albert J. Robichaud · Journal of the American Chemical Society · 1991 · 133 citations

, , +8

A Short Total Synthesis of (±)-Epimeloscine and (±)-Meloscine Enabled by a Cascade Radical Annulation of a Divinylcyclopropane

Hanmo Zhang, Dennis P. Curran · Journal of the American Chemical Society · 2011 · 126 citations

, , +13