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Total Synthesis of Dapholdhamine B and Dapholdhamine B Lactone.

著者 Guo LD , Hou J , Tu W , Zhang Y , Zhang Y , Chen L , Xu J
J Am Chem Soc.2019 Jul 12 ; ():.
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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.
PMID: 31299155 [PubMed - as supplied by publisher]
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