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Total Synthesis of Diterpenoid Steenkrotin A
Author(s) -
Pan Saiyong,
Xuan Jun,
Gao Beiling,
Zhu An,
Ding Hanfeng
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201502034
Subject(s) - aldol reaction , intramolecular force , total synthesis , stereochemistry , chemistry , aldol condensation , olefin fiber , ring (chemistry) , organic chemistry , catalysis
A concise and diastereoselective total synthesis of the diterpenoid (±)‐steenkrotin A is described for the first time. The strategy mainly features three key ring formations: 1) a rhodium‐catalyzed OH bond insertion followed by an intramolecular carbonyl‐ene reaction to build up the tetrahydrofuran subunit; 2) sequential SmI 2 ‐mediated Ueno–Stork and ketyl–olefin cyclizations to construct the [5,7] spirobicyclic skeleton; and 3) an intramolecular aldol condensation/vinylogous retro‐aldol/aldol sequence to form the final six‐membered ring with inversion of the relative configuration at the C7 position.