Toward a modular, bidirectional synthesis of (−)-mucocin

Autor:	Sadagopan Raghavan, S. Ganapathy Subramanian
Rok vydání:	2011
Předmět:	chemistry.chemical_classification Diene Stereochemistry Alkene Organic Chemistry Enantioselective synthesis Epoxide Biochemistry Stereocenter chemistry.chemical_compound chemistry Nucleophile Suzuki reaction Intramolecular force Drug Discovery
Zdroj:	Tetrahedron. 67:7529-7539
ISSN:	0040-4020
DOI:	10.1016/j.tet.2011.07.079
Popis:	A convergent stereoselective synthesis of the C13–C34 fragment of (−)-mucocin is described. The salient features include (a) the bidirectional synthesis of the C-2 symmetric C13–C21 subunit, (b) regio- and stereoselective preparation of a 1,3-diol derivative from a diene activated by NBS via intramolecular nucleophilic sulfinyl group participation, (c) utilizing the self-metathesis reaction to prepare a functionalized C10 alkene, and (d) regio- and stereoselective intermolecular epoxide opening to construct the ether bond between C20 and C24. An organocatalytic α-hydoxylation has been employed to create the C4 stereogenic center of C1–C12 subunit. Attempted union of the two subunits utilizing the B-alkyl Suzuki coupling did not succeed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::cff7dad05b3ba6d698916160cb45cd9c https://doi.org/10.1016/j.tet.2011.07.079 Zobrazit plný text záznamu Full Text from ScienceDirect