| Literature DB >> 11674079 |
Kelly Marshall Aubart1, Clayton H. Heathcock.
Abstract
The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to give enone 46. Bromination at the alpha position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.Entities:
Year: 1999 PMID： 11674079 DOI： 10.1021/jo9815397
Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354