Premium
An Intramolecular Case of Sharpless Kinetic Resolution: Total Synthesis of Laulimalide
Author(s) -
Mulzer Johann,
Öhler Elisabeth
Publication year - 2001
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 - 10.1002/1521-3773(20011015)40:20<3842::aid-anie3842>3.0.co;2-r
Subject(s) - carbon skeleton , intramolecular force , kinetic resolution , regioselectivity , computer science , stereochemistry , ring (chemistry) , chemistry , enantioselective synthesis , organic chemistry , catalysis
The microtubule‐stabilizing antitumor agent laulimalide ( 1 ) has been obtained in by new synthetic route. The carbon skeleton was assembled by means of Julia–Kocienski (C16–C17) and Horner–Wadsworth–Emmons (C21–C22) olefinations. Still–Gennari olefination was used for the C2–C3 ring closure. The key step of the synthesis was a regioselective C16–C17 matched Sharpless asymmetric epoxidation.