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First Synthesis of 12‐Oxosoladulcidine and Its Derivatives as Potential Antitumor Steroidal Alkaloids
Author(s) -
Zha Xiaoming,
Hou Yingwei,
Sun Hongbin,
Zhang Yihua
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790135
Subject(s) - chemistry , stereochemistry , yield (engineering) , combinatorial chemistry , metallurgy , materials science
The first synthesis of 12‐oxosoladulcidine (=(3 β ,5 α ,22 α ,25 R )‐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 ).