Efficient synthesis of solasodine, O-acetylsolasodine, and soladulcidine as anticancer steroidal alkaloids.
An efficient synthesis of the steroidal alkaloids solasodine (1), O-acetylsolasodine (2), and soladulcidine (3) starting from easily available diosgenin and tigogenin in five or six steps (overall yield 25, 24, and 28%, resp.) is described. Moreover, our synthetic route provides a selective modification at C(3) of 1 and related compounds in order to carry out lead optimization on these natural antitumor steroidal alkaloids.
Zha
Xiaoming
X
Center for Drug Discovery, School of Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu Province, 210009, PR China.
Sun
Hongbin
H
Hao
Jia
J
Zhang
Yihua
Y
D000970:Antineoplastic Agents / Q000494:pharmacology*; D010840:Phytosterols / Q000138:chemical synthesis* / Q000494:pharmacology; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D013057:Spectrum Analysis
D000970:Antineoplastic Agents; D010840:Phytosterols; D012991:Solanaceous Alkaloids; C520408:spirosol-5-en-3-yl acetate; C520407:spirosolan-3-ol; C012037:solasodine