First synthesis of 12-oxosoladulcidine and its derivatives as potential antitumor steroidal alkaloids.
The first synthesis of 12-oxosoladulcidine (= (3beta,5alpha,22alpha,25R)-3-hydroxyspirosolan-12-one; 4) is reported, and its structure was confirmed by single-crystal X-ray diffraction analysis. Compound 4 was readily obtained in five steps in an overall yield of 31%, starting from hecogenin (5). By slightly modifying the synthetic protocol, eight analogues of 4 were also prepared. The title compound and its derivatives are expected to be potent antitumor alkaloids, since structurally closely related to the known antitumor agents soladulcidine (2) and hecogenin (5).
Zha
Xiaoming
X
Center for Drug Discovery, School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China.
Hou
Yingwei
Y
Sun
Hongbin
H
Zhang
Yihua
Y
D000470:Alkaloids / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D010840:Phytosterols / Q000138:chemical synthesis*; D012991:Solanaceous Alkaloids / Q000138:chemical synthesis*; D013256:Steroids / Q000138:chemical synthesis*
D000470:Alkaloids; D000970:Antineoplastic Agents; D010840:Phytosterols; D012991:Solanaceous Alkaloids; D013256:Steroids; C520407:spirosolan-3-ol