Synthetic Study of (−)‐Norzoanthamine: Construction of the ABC Ring Moiety | Zendy

Murata Yoshihisa | Zendy; Yamashita Daisuke | Zendy; Kitahara Katsushi | Zendy; Minasako Yohei | Zendy; Nakazaki Atsuo | Zendy; Kobayashi Susumu | Zendy

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Synthetic Study of (−)‐Norzoanthamine: Construction of the ABC Ring Moiety

Author(s) -

Murata Yoshihisa,

Yamashita Daisuke,

Kitahara Katsushi,

Minasako Yohei,

Nakazaki Atsuo,

Kobayashi Susumu

Publication year - 2009

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.200804544

Subject(s) - moiety , ring (chemistry) , decalin , intramolecular force , ketone , stereochemistry , quaternary carbon , chemistry , enantioselective synthesis , organic chemistry , catalysis

Throw your hat in the ring : A highly diastereoselective synthesis of the ABC rings of (−)‐norzoanthamine has been achieved starting from the (−)‐Hajos–Parrish ketone (see scheme). Three asymmetric quaternary carbon centers on the C ring were constructed by a 1,4‐addition, and an intramolecular Diels–Alder reaction provided a trans ‐decalin scaffold on the AB rings.

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