Premium
Total Synthesis of (±)‐Pentalenolactone A Methyl Ester
Author(s) -
Liu Qi,
Yue Guozong,
Wu Na,
Lin Guang,
Li Yuanzhen,
Quan Junmin,
Li Chuangchuang,
Wang Guoxin,
Yang Zhen
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.201206705
Subject(s) - phosphonate , intramolecular force , cyclopentenone , stereoselectivity , trimethylsilyl , chemistry , quaternary carbon , total synthesis , stereochemistry , medicinal chemistry , catalysis , organic chemistry , enantioselective synthesis
Ringing it up : The methyl ester of pentalenolactone A has been obtained through the stereoselective synthesis of a cyclopentenone by a combination of the Co‐mediated Pauson–Khand reaction (PKR) of enyne 1 , and the construction of a quaternary‐carbon‐based strained α‐methylidene‐δ‐pentyrolactone core through a trimethylsilyl (TMS) mediated, telescoped intramolecular Michael olefination (TIMO) reaction of keto‐phosphonate 2 .