z-logo
Premium
Total Synthesis of an Atropisomer of the Schisandra Triterpenoid Schiglautone A
Author(s) -
Ma Binjie,
Zhao Yifan,
He Chi,
Ding Hanfeng
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201809076
Subject(s) - atropisomer , chemistry , stereochemistry , ring (chemistry) , metathesis , ring closing metathesis , enantioselective synthesis , schisandra , epoxide , salt metathesis reaction , combinatorial chemistry , catalysis , organic chemistry , medicine , alternative medicine , traditional chinese medicine , pathology , polymerization , polymer
A diastereoselective approach for the total synthesis of an unusual atropisomer of the Schisandra triterpenoid (±)‐schiglautone A is described. The efficient synthetic strategy features three key transformations: 1) two sequential titanium(III)‐catalyzed radical cyclization/homologation reactions to construct the trans ‐fused [6,7] bicycle as well as install the quaternary carbons at C10 and C14 with the desired stereochemistry; 2) a Claisen rearrangement followed by a ring‐closing metathesis to forge the strained nine‐membered ring; and 3) a substrate‐controlled Michael addition to enable the introduction of the C17 side‐chain with good diastereoselectivity.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here