A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D

Authors
Aubart, KM Heathcock, CH
Citation
Km. Aubart et Ch. Heathcock, A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D, J ORG CHEM, 64(1), 1999, pp. 16-22
Citations number
65
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
1
Year of publication
1999
Pages
16 - 22
Database
ISI
SICI code
0022-3263(19990108)64:1<16:ABATTD>2.0.ZU;2-W
Abstract
The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tryramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cycliz ation provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to gi ve enone 46. Bromination at the a position gives a mixture of bromoenones t hat undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment wi th basic alumina.