4.6 Article

Divergent Total Syntheses of (-)-Huperzine Q, (+)-Lycopladine B, (+)-Lycopladine C, and (-)-4-epi-Lycopladine D

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 12, Issue 13, Pages 1557-1567

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201700364

Keywords

aldol reaction; alkaloids; metathesis; natural products; total synthesis

Funding

  1. National Natural Science Foundation of China (NNSFC) [21625201, 21561142002, 21472010]
  2. National High Technology Projects 973 [2015CB856200]

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We report herein our synthetic efforts towards the divergent syntheses of (-)-huperzine Q (1), (+)-lycopladine B (2), (+)-lycopladine C (3), and (-)-lycopladine D (4). The 10-step total synthesis of (-)-huperzine Q (1) and the first total syntheses of (+)-lycopladines B (2) and C (3) were accomplished through a series of cascade reactions. Our approach involved a Michael addition/aldol/intramolecular C-alkylation sequence to forge the 6/9 spirocycle ring, and this was followed by an ethylene-accelerated carbonyl-olefin metathesis to construct the common 6/5/9 ring system. Finally, latestage enamine bromofunctionalization enabled us to access (-)-huperzine Q (1), (+)-lycopladine B (2), and (+)-lycopladine C (3), and a tandem C4-epimerization/retro-Claisen condensation furnished (-)-4-epi-lycopladine D (63).

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