Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A.

Subba Reddy, B V; Biradar, Dhanraj O; Vikram Reddy, Y; Yadav, J S; Singarapu, Kiran Kumar; Sridhar, B

Subba Reddy, B V; Biradar, Dhanraj O; Vikram Reddy, Y; Yadav, J S; Singarapu, Kiran Kumar; Sridhar, B.

Afiliación

Subba Reddy BV; Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
Biradar DO; Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
Vikram Reddy Y; Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
Yadav JS; Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
Singarapu KK; Centre for Nuclear Magnetic Resonance, Hyderabad -500 007, India.
Sridhar B; Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad -500 007, India.

Org Biomol Chem ; 14(37): 8832-8837, 2016 Sep 21.

Article en En | MEDLINE | ID: mdl-27714240

RESUMEN

A novel bicyclization strategy has been developed for the stereoselective synthesis of bicyclic lactones, i.e. 7-aryl or alkyl-2,6-dioxabicyclo[3.3.1]nonan-3-ones through a domino cyclization of (R)-3-hydroxyhex-5-enoic acid with an aldehyde in the presence of 10 mol% trimethylsilyltriflate under mild conditions. The salient features of this methodology are high yields, excellent selectivity, low catalyst loading and faster reaction times. This method has been successfully applied to the total synthesis of pyranopyran, tetraketide and polyrhacitide A.

Asunto(s)

Compuestos Bicíclicos Heterocíclicos con Puentes/síntesis química; Ciclohexanonas/síntesis química; Disacáridos/síntesis química; Lactonas/síntesis química; Piranos/síntesis química; Aldehídos/síntesis química; Aldehídos/química; Compuestos Bicíclicos Heterocíclicos con Puentes/química; Catálisis; Ciclización; Ciclohexanonas/química; Disacáridos/química; Lactonas/química; Modelos Moleculares; Piranos/química; Estereoisomerismo; Compuestos de Trimetilsililo/síntesis química; Compuestos de Trimetilsililo/química

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Piranos / Compuestos Bicíclicos Heterocíclicos con Puentes / Ciclohexanonas / Disacáridos / Lactonas Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2016 Tipo del documento: Article País de afiliación: India Pais de publicación: Reino Unido

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