Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052).

Ling, Taotao; Macherla, Venkat R; Manam, Rama Rao; McArthur, Katherine A; Potts, Barbara C M

Ling, Taotao; Macherla, Venkat R; Manam, Rama Rao; McArthur, Katherine A; Potts, Barbara C M.

Afiliación

Ling T; Nereus Pharmaceuticals, Inc., 10480 Wateridge Circle, San Diego, California 92121, USA.

Org Lett ; 9(12): 2289-92, 2007 Jun 07.

Article en En | MEDLINE | ID: mdl-17497868

ABSTRACT

ABSTRACT

A novel enantioselective total synthesis of 20S proteasome inhibitor Salinosporamide A (NPI-0052; 1) is presented. Key features include intramolecular aldol cyclization of 6 to simultaneously generate the three chiral centers of advanced intermediate 5, cyclohexene ring addition using B-2-cyclohexen-1-yl-9-BBN, and inversion of the C-5 stereocenter by oxidation followed by enantioselective enzymatic reduction.

Asunto(s)

Lactonas/síntesis química; Pirroles/síntesis química; Cristalografía por Rayos X; Lactonas/química; Modelos Moleculares; Conformación Molecular; Pirroles/química; Estereoisomerismo

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pirroles / Lactonas Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2007 Tipo del documento: Article País de afiliación: Estados Unidos

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