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A Catalytic Asymmetric Three-Component 1,4-Addition/Aldol Reaction: Enantioselective Synthesis of the Spirocyclic System of Vannusal A

✍ Scribed by K. C. Nicolaou; Wenjun Tang; Philippe Dagneau; Raffaella Faraoni

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
355 KB
Volume
117
Category
Article
ISSN
0044-8249

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✦ Synopsis

The advantages of multicomponent reactions over the more common two-component processes have been widely demonstrated and reviewed. [1] Efficient asymmetric versions of such reactions offer even greater benefits to the art of chemical synthesis, as these can provide expedient access to polyfunctionalized molecules in enantioenriched form, starting from simple prochiral building blocks. [2, 3] During a program directed towards the total synthesis of vannusal A (1, Scheme 1), an architecturally complex marine natural product isolated from the ciliate Euplotes vannus, [4] the key optically enriched spirocyclic intermediate 2 was required. This demand led us to the development of an asymmetric multicomponent reaction that combined a,b-unsaturated

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