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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.