Results
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