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Org Lett. 2018 Oct 5;20(19):6121-6125. doi: 10.1021/acs.orglett.8b02568. Epub 2018 Sep 20.

Asymmetric Cα-Alkylation of Proline via Chirality Transfers of Conformationally Restricted Proline Derivative: Application to the Total Synthesis of (-)-Amathaspiramide F.

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1
College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu, Seoul 08826 , Korea.

Abstract

An efficient strategy for the asymmetric synthesis of Cα-tetrasubstituted proline derivatives from proline has been established. A nitrogen-fused bicyclic system was devised to control the stereodynamics of proline. Through N-quaternizations with allylic electrophiles followed by [2,3]-rearrangements, the bicyclic proline system delivered enantioenriched Cα-tetrasubstituted prolines. This strategy was applied to the concise total synthesis of (-)-amathaspiramide F.

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