Concise total synthesis of (-)-spongotine A

Kenichi Murai; Maiko Morishita; Ryo Nakatani; Ozora Kubo; Hiromichi Fujioka; Yasuyuki Kita

doi:10.1021/jo701668s

Concise total synthesis of (-)-spongotine A

J Org Chem. 2007 Nov 9;72(23):8947-9. doi: 10.1021/jo701668s. Epub 2007 Oct 12.

Authors

Kenichi Murai¹, Maiko Morishita, Ryo Nakatani, Ozora Kubo, Hiromichi Fujioka, Yasuyuki Kita

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-Oka, Suita, Osaka, Japan.

PMID: 17929980
DOI: 10.1021/jo701668s

Abstract

The first asymmetric total synthesis of spongotine A is described. The oxidative synthesis of the imidazoline/ketone unit from keto aldehyde and diamine is a key step in this synthesis. The absolute stereochemistry of the asymmetric center of natural spongotine A is revealed as the (S)-configuration.

Publication types

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

MeSH terms

Combinatorial Chemistry Techniques
Imidazolines / chemical synthesis*
Imidazolines / chemistry
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Stereoisomerism

Substances

Imidazolines
Indole Alkaloids
spongotine A