Novel use of a selenoalkyne within untraditionally mild Dotz benzannulation processes; Total synthesis of a Calceolaria andina L. natural hydroxylated naphthoquinone

Authors
Caldwell, JJ Colman, R Kerr, WJ Magennis, EJ
Citation
Jj. Caldwell et al., Novel use of a selenoalkyne within untraditionally mild Dotz benzannulation processes; Total synthesis of a Calceolaria andina L. natural hydroxylated naphthoquinone, SYNLETT, (9), 2001, pp. 1428-1430
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
9
Year of publication
2001
Pages
1428 - 1430
Database
ISI
SICI code
0936-5214(200109):9<1428:NUOASW>2.0.ZU;2-U
Abstract
A total synthesis of the Calceolaria andina L. extract 2-(1,1-dimethyl-2-pr openyl)-3-hydroxy-1,4-naphthalenedione is described incorporating the first reported Dotz benzannulation of a selenoalkyne. Importantly, it has been s hown that it is possible to effect this annulation at ambient temperature u nder dry state conditions with a significant improvement in cyclisation yie ld.