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Enantioselective Synthesis of the Spirotetracyclic Carbon Core of Mangicols by Using a Stereoselective Transannular Diels–Alder Strategy
Author(s) -
Araki Keisuke,
Saito Keiji,
Arimoto Hirokazu,
Uemura Daisuke
Publication year - 2003
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.200351750
Subject(s) - enantioselective synthesis , intramolecular force , stereoselectivity , diels–alder reaction , chemistry , core (optical fiber) , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , materials science , composite material
“TADA!” is not the trumpet fanfare but the transannular Diels–Alder reaction concluding the synthesis of the tetracyclic core of the mangicols, a family of marine sesterterpenes. Further highlights in the synthesis include a novel chlorination and an intramolecular Nozaki–Hiyama–Kishi coupling reaction. Bn=benzyl.