Bioinspired Total Synthesis and Stereochemical Revision of the Fungal Metabolite Pestalospirane B.

Badrinarayanan, Sandhya; Squire, Christopher J; Sperry, Jonathan; Brimble, Margaret A

Badrinarayanan, Sandhya; Squire, Christopher J; Sperry, Jonathan; Brimble, Margaret A.

Afiliação

Badrinarayanan S; School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
Squire CJ; School of Biological Sciences, University of Auckland , 3A Symonds Street, Auckland, New Zealand.
Sperry J; School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
Brimble MA; School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.

Org Lett ; 19(13): 3414-3417, 2017 07 07.

Article em En | MEDLINE | ID: mdl-28621951

ABSTRACT

ABSTRACT

The total synthesis of both enantiomers of pestalospirane B, 2, has been achieved using a bioinspired tandem dimerization-spiroketalization reaction. Electronic circular dichroism (ECD) and X-ray analysis were used to revise the absolute stereochemistry of the natural product pestalospirane B from 3S, 3'S, 12R, 12'R to its enantiomer 3R, 3'R, 12S, 12'S.

Assuntos

Benzoxepinas/química; Compostos de Espiro/química; Dicroísmo Circular; Estrutura Molecular; Estereoisomerismo; Xantofilas

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Compostos de Espiro / Benzoxepinas Idioma: En Revista: Org Lett Ano de publicação: 2017 Tipo de documento: Article

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