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Total Synthesis of (−)‐13‐Oxyingenol and its Natural Derivative
Author(s) -
Ohyoshi Takayuki,
Funakubo Shota,
Miyazawa Yamato,
Niida Keisuke,
Hayakawa Ichiro,
Kigoshi Hideo
Publication year - 2012
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.201201383
Subject(s) - derivative (finance) , total synthesis , ring (chemistry) , olefin metathesis , closing (real estate) , metathesis , stereochemistry , computer science , chemistry , combinatorial chemistry , organic chemistry , political science , business , polymerization , polymer , finance , law
Ring functionalization : The total synthesis of a natural derivative of (−)‐13‐oxyingenol, a potent anti‐HIV diterpenoid, is reported. The key steps in this synthesis include a ring‐closing olefin metathesis and a Mislow–Evans‐type [2,3]‐sigmatropic rearrangement. This synthesis provides access to (−)‐13‐oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co‐workers.