Geissman-Waiss lactone

Cbz-4-hydroxy-L-proline was used in the preparation of 72 (the Geissman-Waiss lactone), which is a synthon for necines (82H23). This compound was prepared in eight steps (62JOC139). The alkaloids retronecine, platy-necine, and croalbinecine were prepared from the lactone (83H1331). 

The Geissman-Waiss lactone (7)( ) is a well-known precursor of (+)- retronecine ( ) ( -y-), one of the most common necine bases... 

An identical series of reactions starting with 959b yields the protected A -(2-hydroxyethyl) Geissman-Waiss lactone 964b [210]. Either of the lactones 964 is readily converted to ( + )-retronecine (883), as shown in Scheme 142. 

The conditions for related reactions were optimized by Yoshida and co-woricers (Scheme 27). The formation of lactones 15 proceeds similar to the reaction shown in Scheme The choice of solvent was found to be crucial under standard conditions, as used for alkoxycarbonylations (Scheme 27, conditions A), piperazine side products 16 are formed. However, in acetic acid (procedure B) this side reaction is suppressed and the desired products (15) are obtained in high yield. This chemistry has found application in syntheses of the Geissman-Waiss lactone and of 1,4-iminoglycitols. " ... 

Oxa-6-azabicyclo[3.3.0]octan-3-one. 3-Hydroxypyrrolidine-2-acetic acid lactone. Geissman- Waiss lactone... 

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 ... 

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