Macrocyclic lactam synthesis via a ring expansion reaction: construction of the cripowellin skeleton

Bongjin Moon; Sangbae Han; Yeojin Yoon; Hyejin Kwon

doi:10.1021/ol047520+

Macrocyclic lactam synthesis via a ring expansion reaction: construction of the cripowellin skeleton

Org Lett. 2005 Mar 17;7(6):1031-4. doi: 10.1021/ol047520+.

Authors

Bongjin Moon¹, Sangbae Han, Yeojin Yoon, Hyejin Kwon

Affiliation

¹ Department of Chemistry, Sogang University, Seoul 121-742, Korea. bjmoon@ccs.sogang.ac.kr

PMID: 15760131
DOI: 10.1021/ol047520+

Abstract

[reaction: see text] The cripowellin ring skeleton, a macrocyclic [2.3.5]-bicyclic ketolactam, was smoothly generated via construction of a spiro(benzazepin-cyclohexane-1,3-dione) employing oxidative cyclization as a key step and a subsequent ring expansion reaction.

Publication types

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

MeSH terms

Amaryllidaceae Alkaloids / chemical synthesis*
Amaryllidaceae Alkaloids / chemistry
Catalysis
Cyclization
Indicators and Reagents
Lactams, Macrocyclic / chemical synthesis*
Molecular Structure
Oxidation-Reduction
Plants, Medicinal / chemistry

Substances

Amaryllidaceae Alkaloids
Indicators and Reagents
Lactams, Macrocyclic
cripowellin A
cripowellin B