Premium
Light‐Mediated Total Synthesis of 17‐Deoxyprovidencin
Author(s) -
Toelle Nina,
Weinstabl Harald,
Gaich Tanja,
Mulzer Johann
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400617
Subject(s) - isomerization , aldol reaction , stereochemistry , chemistry , furan , ring (chemistry) , ring closing metathesis , metathesis , stereoselectivity , total synthesis , epoxide , catalysis , organic chemistry , polymerization , polymer
An asymmetric synthesis of the diterpenoid 17‐deoxyprovidencin is described. Key steps include an aldol addition, a base‐catalyzed Wipf‐type furan formation, a Z ‐selective ring‐closing metathesis for macrocyclization, a photochemical E / Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.