Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration.

Ohtsuki, Keiko; Matsuo, Kazumasa; Yoshikawa, Takashi; Moriya, Chihiro; Tomita-Yokotani, Kaori; Shishido, Kozo; Shindo, Mitsuru

Ohtsuki, Keiko; Matsuo, Kazumasa; Yoshikawa, Takashi; Moriya, Chihiro; Tomita-Yokotani, Kaori; Shishido, Kozo; Shindo, Mitsuru.

Afiliación

Ohtsuki K; Institute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasugako-en, Kasuga 816-8580, Japan.

Org Lett ; 10(6): 1247-50, 2008 Mar 20.

Article en En | MEDLINE | ID: mdl-18288857

RESUMEN

Intramolecular acylation of an organolithium leads to an efficient stereocontrolled total synthesis of both enantiomers of sundiversifolide. The absolute configuration was determined by HPLC analysis and allelopathy assay. The gamma-lactone moiety resulted from a butenolide was obtained by the condensation of a bicyclic alpha-hydroxyhemiacetal with Ph3P=CMe(CO2R).

Asunto(s)

Xantenos/síntesis química; Acilación; Estructura Molecular; Xantenos/química

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Xantenos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2008 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

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