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Convergent Synthesis of Solamargine and Analogues Thereof: Structural Revision of 16‐ epi ‐Solamargine and Cytotoxic Evaluation
Author(s) -
Chen Pengwei,
Wang Peng,
Liu Li,
Qiu Peiju,
Zhang Lijuan,
Song Ni,
Ren Sumei,
Guan Huashi,
Li Ming
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500302
Subject(s) - chemistry , stereochemistry , stereoselectivity , cytotoxicity , hydrochloride , protonation , convergent synthesis , nitrogen atom , biochemistry , in vitro , catalysis , organic chemistry , alkyl , ion
An effective and stereoselective protocol for convergent synthesis of solamargine, a representative of spirosolane‐type glycoalkaloids, is reported. HB(C 6 F 5 ) 4 ‐catalyzed coupling of 26‐azido‐pseudodiosgenin with chacotriosyl trichloroacetimidate as the key step for synthesis of solamargine proceeded in high yield and with excellent stereoselectivity. Three analogues of solamargine were synthesized by the method. Protonation of the nitrogen atom by deuterium chloride had a significant influence on the 1 H NMR spectrum of solamargine. On the basis of these results, the structure of 16‐ epi ‐solamargine was revised to solamargine hydrochloride. The cytotoxicity of solamargine together with its analogues against cancer cell lines was evaluated.