Stereoselective Chemoenzymatic Cascade Synthesis of the bis -THF Core of Acetogenins

Autor:	Matthijs J. van Lint, Kurt Faber, Rob J.M. van Spanning, Romano V. A. Orru, Eelco Ruijter, Mélanie Hall
Rok vydání:	2018
Předmět:	010405 organic chemistry Stereochemistry Organic Chemistry Epoxide 010402 general chemistry 01 natural sciences Desymmetrization 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Cascade Epoxide Hydrolases Stereoselectivity Physical and Theoretical Chemistry Bullatacin
Zdroj:	European Journal of Organic Chemistry. 2019:1092-1101
ISSN:	1434-193X
DOI:	10.1002/ejoc.201801562
Popis:	bis-Tetrahydrofuran acetogenins are a class of natural products displaying highly potent and selective anti-tumor activity. Herein we report a new route to precursors of these natural products, utilizing the pseudo C2-symmetry in the central bis-tetrahydrofuran fragment. Key steps of our stereoselective chemoenzymatic strategy include the epoxide hydrolase-mediated desymmetrization of meso-epoxides and a cascade cyclization in either “inside-out” or “outside-in” direction, providing stereoselective access to the cores of both bullatacin- and rolliniastatin 1-type acetogenins with 6 stereocenters each from a common mono-epoxide precursor.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9f1fa985a2580e66d2be65ad68c7bccf https://doi.org/10.1002/ejoc.201801562 Zobrazit plný text záznamu