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Total Synthesis of (+)‐Epoxyquinols A and B
Author(s) -
Shoji Mitsuru,
Yamaguchi Junichiro,
Kakeya Hideaki,
Osada Hiroyuki,
Hayashi Yujiro
Publication year - 2002
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(20020902)41:17<3192::aid-anie3192>3.0.co;2-e
Subject(s) - furan , stereoselectivity , total synthesis , chemistry , acrylate , monomer , diels–alder reaction , stereochemistry , organic chemistry , catalysis , polymer
A highly stereoselective HfCl 4 ‐mediated Diels–Alder reaction of furan and the chiral acrylate ester of Corey's auxiliary to subsequently give 1 , and the realization of the postulated biosynthetic pathway for the construction of epoxyquinols A and B, namely, oxidative 6π electrocyclization, followed by Diels–Alder reaction of the unprotected monomer are the key steps in the asymmetric total synthesis of (+)‐epoxyquinols A and B.