Lipase-catalyzed asymmetric demethoxycarbonylation: Formal syntheses of (+)-carbacyclin, (−)-ajmalicine, and (−)-tetrahydroalstonine

Autor:	T. Inoue, Mamoru Araki, Manabu Node, Daisaku Nakamura, Kiyoharu Nishide
Rok vydání:	1998
Předmět:	Ajmalicine biology Organic Chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Tetrahydroalstonine biology.protein Organic chemistry Physical and Theoretical Chemistry Lipase Enantiomer
Zdroj:	Tetrahedron: Asymmetry. 9:157-167
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(97)00616-2
Popis:	Both enantiomers of C 2 -symmetric dimethyl 3,7-dihydroxybicyclo[3.3.0]-octa-2,6-diene-2,6-dicarboxylate 3 were prepared in enantiomerically pure form from symmetric tetraester 1 by the lipase-catalyzed demethoxycarbonylation, respectively. Double asymmetric differentiation with lipase in the above demethoxycarbonylation was observed. Their applications to formal total syntheses of (+)-carbacyclin and (−)-ajmalicine including (−)-tetrahydroalstonine are also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::cee13e0d6b39248b4107f61b2409236e https://doi.org/10.1016/s0957-4166(97)00616-2 Zobrazit plný text záznamu Full Text from ScienceDirect