4.8 Article

Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 2, Pages 637-640

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610484

Keywords

biomimetic synthesis; cycloaddition; natural products; terpenoids; total synthesis

Funding

  1. NSFC [21290180, 21322205, 21321061, 21672153]
  2. Open Fund of State Key Laboratory of Natural Medicines in China Pharmaceutical University [SKLNMKF201601]

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The syntheses of members of a family of lindenane sesquiterpenoid [4+ 2] dimers led to the total syntheses of sarcandrolide J and shizukaol D. Inspired by a modified biosynthetic pathway, a cascade featuring furan formation/alkene isomerization/Diels-Alder cycloaddition was devised to construct the congested polycyclic architecture of the target molecules with the correct stereochemistry. This study presents a pioneering synthetic entry to this family of natural products and paves the way for fully exploring their biological functions.

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