Synthetic study of (-)-norzoanthamine: construction of the ABC ring moiety.
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.
Murata
Yoshihisa
Y
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba, Japan.
Yamashita
Daisuke
D
Kitahara
Katsushi
K
Minasako
Yohei
Y
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D011804:Quinolines; C400280:norzoanthamine