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- Title
Concise total syntheses of lysergene, lysergine, isolysergine and festuclavine.
- Authors
Tasker, Nikhil R.; Wipf, Peter
- Abstract
A streamlined synthesis of the tetracyclic ergot alkaloid scaffold enabled the preparation of several clavine alkaloids, including lysergol, isolysergol, lysergine, isolysergine, lysergene, and festuclavine. The mesylation and subsquent elimination or reduction of lysergol and isolysergol building blocks complements and expands previous total syntheses of these natural products. In the course of the preparation of isolysergine, an interesting new cascade process was discovered that led to the formation of a cyclopropanated ergolin-2(3H)- one as a spontaneous oxidation product of an intermediate 1,3-dihydrobenzo[cd]indole.
- Subjects
ERGOT alkaloids; NATURAL products; INDOLE; OXIDATION
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2024, Vol 2024, p1
- ISSN
1551-7004
- Publication type
Academic Journal
- DOI
10.24820/ark.5550190.p012.120