ChemInform Abstract: Total Syntheses of (-)-Isoschizogamine and (-)-2-Hydroxyisoschizogamine

Autor:	Ling Tan, Xiaobei Wang, Hongxiu Huang, Huan Chen, Yong Qin, Hao Song, Dongliang Xia
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Hydrolysis chemistry chemistry.chemical_element Regioselectivity General Medicine Isoschizogamine Oxygen Medicinal chemistry Enamine Quaternary carbon
Zdroj:	ChemInform. 46
ISSN:	0931-7597
DOI:	10.1002/chin.201548196
Popis:	Total syntheses of (-)-isoschizogamine and (-)-2-hydroxyisoschizogamine are described. The synthesis employs two asymmetric Michael additions to establish chiral centers at C7 and the quaternary carbon C20. Regioselective reduction of the methylthioiminium cation rather than the enamine generates an isoschizogamine-type pentacyclic skeleton. Acidic hydrolysis of the isoschizogamine-type intermediate in the absence of oxygen provides natural (-)-isoschizogamine. Conducting the reaction in the presence of oxygen leads to a multistep oxidative hydrolysis cascade that affords unnatural (-)-2-hydroxyisoschizogamine.
Databáze:	OpenAIRE
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