Total Synthesis of Dapholdhamine B and Dapholdhamine B Lactone.

08:00 EDT 12th July 2019 | BioPortfolio

Summary of "Total Synthesis of Dapholdhamine B and Dapholdhamine B Lactone."

The intriguing structural complexity and bioactivities of the alkaloids have long attracted much attention. Herein, we report the first and enantioselective total synthesis of alkaloid dapholdhamine B and its lactone derivative. The chemical structure of dapholdhamine B contains a unique aza-adamantane core skeleton and eight contiguous stereocenters, including three contiguous fully substituted stereocenters, which present a formidable synthetic challenge. This concise approach used to achieve the first synthesis of an aza-adamantane natural product features a vinylogous Mannich reaction, an optimized α-bromo-α,β-unsaturated ketone synthesis, a substrate-dependent intramolecular aza-Michael addition, a key annulation via amide activation, an S2'-type lactonization, and a facile Horner-Wadsworth-Emmons reaction that converts the hemiacetal moiety to the corresponding homologated carboxylic acid.


Journal Details

This article was published in the following journal.

Name: Journal of the American Chemical Society
ISSN: 1520-5126


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