Convergent stereospecific total synthesis of monochiral Monocillin I related macrolides

Autor:	Robert Lett, Maxime Lampilas
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Ketone Stereochemistry Organic Chemistry chemistry.chemical_element Epoxide Total synthesis Biochemistry Isocoumarin chemistry.chemical_compound Stereospecificity chemistry Drug Discovery Mitsunobu reaction Lactone Palladium
Zdroj:	Tetrahedron Letters. 33:773-776
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)77712-4
Popis:	The first total synthesis of Monocillin I related macrolides has been achieved by a convergent and stereospecific route involving the palladium - catalyzed coupling of a functionnalized chiral vinylstannane with the appropriate dimethoxy bromomethyl isocoumarin. Cleavage conditions of the isocoumarin ring were then found for the preparation of a precursor hydroxy acid. The 14-membered macrolide was obtained in the Mitsunobu reaction conditions, and the required natural conjugated dienone epoxide system of Monocillin I was generated stereospecifically from that macrocyclic precursor.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ff08485c11ae380645b03e49558a1312 https://doi.org/10.1016/s0040-4039(00)77712-4 Zobrazit plný text záznamu