Rhodium-catalyzed endo-selective epoxide-opening cascades: formal synthesis of (-)-brevisin.

Autor:	Armbrust KW; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States., Beaver MG; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States., Jamison TF; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2015 Jun 03; Vol. 137 (21), pp. 6941-6. Date of Electronic Publication: 2015 May 18.
DOI:	10.1021/jacs.5b03570
Abstrakt:	[Rh(CO)2Cl]2 is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Syntheses of the ABC and EF ring systems of (-)-brevisin via all endo-diepoxide-opening cascades using this method constitute a formal total synthesis and demonstrate the utility of this methodology in the context of the synthesis of marine ladder polyether natural products.
Databáze:	MEDLINE
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