Enantioselective Synthesis of the Spirotetracyclic Carbon Core of Mangicols by Using a Stereoselective Transannular Diels–Alder Strategy | Zendy

Araki Keisuke | Zendy; Saito Keiji | Zendy; Arimoto Hirokazu | Zendy; Uemura Daisuke | Zendy

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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.

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