Employment of a cyclobutene ring-opening metathesis reaction towards a concise synthesis of (+/-)-sporochnol A

Authors
Bassindale, MJ Hamley, P Harrity, JPA
Citation
Mj. Bassindale et al., Employment of a cyclobutene ring-opening metathesis reaction towards a concise synthesis of (+/-)-sporochnol A, TETRAHEDR L, 42(51), 2001, pp. 9055-9057
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
51
Year of publication
2001
Pages
9055 - 9057
Database
ISI
SICI code
0040-4039(200112)42:51<9055:EOACRM>2.0.ZU;2-J
Abstract
A concise formal synthesis of (+/-)-sporochnol A 1, a naturally occurring f eeding deterrent towards herbivorous fish, is described. The target compoun d was prepared by the employment of a Ru-catalysed cyclobutene ring-opening metathesis reaction with gaseous ethylene followed by a site selective hyd roboration reaction as the key steps. The optimisation of the metathesis pr ocess regarding the Ru-catalyst and reaction conditions is also delineated. (C) 2001 Elsevier Science Ltd. All rights reserved.