An unusual intramolecular hetero-Diels-Alder cycloaddition.

Stoner, Eric J; Allen, Michael S; Christesen, Alan C; Henry, Rodger F; Hollis, L Steven; Keyes, Robert; Marsden, Ian; Rehm, Tamara C; Shiroor, Sandeep G; Soni, Niru B; Stewart, Kent D

Stoner, Eric J; Allen, Michael S; Christesen, Alan C; Henry, Rodger F; Hollis, L Steven; Keyes, Robert; Marsden, Ian; Rehm, Tamara C; Shiroor, Sandeep G; Soni, Niru B; Stewart, Kent D.

Afiliação

Stoner EJ; Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064-6290, USA. eric.stoner@abbott.com

J Org Chem ; 70(8): 3332-5, 2005 Apr 15.

Article em En | MEDLINE | ID: mdl-15823010

ABSTRACT

ABSTRACT

A new reaction of erythronolides, an intramolecular hetero-Diels-Alder, has been discovered. Heated aqueous alcoholic solutions of ABT-773 (1) and its cis isomer (3) convert slowly to cycloadducts 2 and 4, respectively. Optimal reaction conditions, mechanistic studies supported by molecular modeling, and biological activity data are reported. Single-crystal X-ray structures for both adducts 2 and 4 have been obtained.

Assuntos

Eritromicina/análogos & derivados; Eritromicina/química; Cetolídeos/química; Catálise; Cristalografia por Raios X; Ciclização; Conformação Molecular; Estrutura Molecular; Estereoisomerismo

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Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Eritromicina / Cetolídeos Idioma: En Revista: J Org Chem Ano de publicação: 2005 Tipo de documento: Article

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