Geissman-Waiss lactone, synthesis

The influence of the functional groups of the substrate in the course of an allylsilane addition to a carbonyl group are exempHfied in the enantiodivergent synthesis of the Geissman-Waiss lactone [63]. The Geissman-Waiss [64] lactone 200 and 202 serves as a versatile intermediate for the synthesis of pyrroUzidine alkaloids. For this reason, there are a variety of different syntheses to this building block [65]. The Geissmann-Waiss lactone synthesis of Wistrand and coworkers not only provides a short access to one enantiomer but also enables the synthesis of both enantiomeric forms. The synthesis is depicted in Scheme 3.40. 

Scheme 3.40 A short, enantiodivergent synthesis of the Geissman-Waiss lactone.

Enantioselective synthesis of (-)-Geissman-Waiss lactone, antituber-cular y-butyrolactones and tetrapeptide derivatives. Abstracts of Papers, 242nd ACS National Meeting and Exposition, Denver, Colorado, August 28-September 1, 2011, p. ORGN-112 ... 

Geissman and Waiss (i<3 )have effected the first stereospecific synthesis of retronecine (CXLIV in 1) by a series of reactions which is shown in Chart I. Ethyl A-carbethoxy-3-aminopropionate (LI) was added to diethyl fumarate and the product ring-closed to the pyrrolidone, LII, which on hydrolysis and reduction yielded the required 3-hydroxy-pyrrolidine-2-acetic acid lactone (LIII). Reaction of this lactone with ethyl bromoacetate gave the A-acetic ester, LIV which by ring closure... 

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