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Stereoselective Synthesis of the Spirocyclic γ-Lactam Core of the Ansalactams. | LitMetric

Stereoselective Synthesis of the Spirocyclic γ-Lactam Core of the Ansalactams.

Org Lett

Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27607, United States.

Published: December 2021


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Article Abstract

Ansalactam A is an ansa macrolide natural product that contains a densely functionalized spiro-γ-lactam core containing three contiguous stereocenters. This unusual motif distinguishes it from other members of this family and represents a significant synthetic challenge. Herein, we report the development of a stereoselective formal [3+2] cycloaddition reaction for the construction of this key spiro-γ-lactam motif for the first time, thereby enabling access to the northern domain of ansalactam A.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9437948PMC
http://dx.doi.org/10.1021/acs.orglett.1c03782DOI Listing

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