A short multigram asymmetric synthesis of prostanoid scaffolds

Depré, Dominique;Chen, Lian-Yong;Ghosez, Léon
(2003) Tetrahedron — Vol. 59, n° 35, p. 6797-6812 (2003)

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  • Depré, DominiqueUCLouvain
    Author
  • Chen, Lian-YongUCLouvain
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
Enantiomerically pure polysubstituted cyclopentanes which can be regarded as prostanoid scaffolds have been prepared by an efficient synthetic sequence readily applicable to the preparation of multigram quantities. The first key reaction is the diastereoselective allylmetallation of oxoamide 4 which is readily prepared from gamma-butyrolactone and an enantiomerically pure 2,5-dimethylpyrrolidine. The second key-step is an intramolecular [2+2] cycloaddition of a keteneiminium salt leading to bicylo[3.2.0] heptanones. These intermediates have been easily transformed into a variety of prostanoid scaffolds of high enantionneric purities. (C) 2003 Elsevier Ltd. All rights reserved.
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Depré, D., Chen, L.-Y., & Ghosez, L. (2003). A short multigram asymmetric synthesis of prostanoid scaffolds. Tetrahedron, 59(35), 6797-6812. https://doi.org/10.1016/S0040-4020(03)00920-7 (Original work published 2003)