Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group

Shinsuke Inuki; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno

doi:10.1021/ol8022648

Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group

Org Lett. 2008 Nov 20;10(22):5239-42. doi: 10.1021/ol8022648. Epub 2008 Oct 29.

Authors

Shinsuke Inuki¹, Shinya Oishi, Nobutaka Fujii, Hiroaki Ohno

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Kyoto, Japan.

PMID: 18956869
DOI: 10.1021/ol8022648

Abstract

Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthesis of (+/-)-lysergic acid, (+/-)-lysergol, and (+/-)-isolysergol was achieved.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes / chemistry*
Bromine / chemistry*
Catalysis
Cyclization
Ergolines / chemical synthesis*
Indoles / chemistry*
Lysergic Acid / chemical synthesis*
Lysergic Acid / chemistry
Palladium / chemistry*
Stereoisomerism

Substances

Alkadienes
Ergolines
Indoles
propadiene
Palladium
Lysergic Acid
lysergol
Bromine