Synthesis 2013; 45(5): 625-632
DOI: 10.1055/s-0032-1318113
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Muricatacin from Tri-O-acetyl-d-glucal

Maria González
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   Email: yagamare@uvigo.es   Email: ggomez@uvigo.es
,
Zoila Gándara
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   Email: yagamare@uvigo.es   Email: ggomez@uvigo.es
,
Gonzalo Pazos
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   Email: yagamare@uvigo.es   Email: ggomez@uvigo.es
,
Generosa Gómez*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   Email: yagamare@uvigo.es   Email: ggomez@uvigo.es
,
Yagamare Fall*
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain   Fax: +34(986)812262   Email: yagamare@uvigo.es   Email: ggomez@uvigo.es
› Author Affiliations
Further Information

Publication History

Received: 19 October 2012

Accepted after revision: 28 December 2012

Publication Date:
05 February 2013 (online)


Abstract

The total synthesis of (–)-muricatacin is achieved using commercially available tri-O-acetyl-d-glucal as the starting material. The structure of the intermediate chiral butenolide is established unambiguously by X-ray crystallographic analysis, which consequently leads to correction of a previous structural misassignment.

Supporting Information