Total synthesis of (-)-norzoanthamine.
No bones about it: (-)-Norzoanthamine, a promising candidate for an anti-osteoporotic drug, was the target of a total synthesis (see scheme). The final bisaminal formation with AcOH/H(2)O gave the DEFG ring, while the cyclization precursor was prepared by installing the remaining bisaminal unit after oxidative cleavage of the cyclopentanol moiety.
Yamashita
Daisuke
D
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba, Japan.
Murata
Yoshihisa
Y
Hikage
Naotsuka
N
Takao
Ken-Ichi
K
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D003517:Cyclopentanes; D006576:Heterocyclic Compounds, 4 or More Rings; D007659:Ketones; D011804:Quinolines; C400280:norzoanthamine; C016327:cyclopentanol