Total synthesis and determination of the absolute configuration of (-)-idesolide

Hiroyuki Yamakoshi; Masatoshi Shibuya; Masaki Tomizawa; Yuji Osada; Naoki Kanoh; Yoshiharu Iwabuchi

doi:10.1021/ol9029676

Total synthesis and determination of the absolute configuration of (-)-idesolide

Org Lett. 2010 Mar 5;12(5):980-3. doi: 10.1021/ol9029676.

Authors

Hiroyuki Yamakoshi¹, Masatoshi Shibuya, Masaki Tomizawa, Yuji Osada, Naoki Kanoh, Yoshiharu Iwabuchi

Affiliation

¹ Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.

PMID: 20136117
DOI: 10.1021/ol9029676

Abstract

The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)-4-Bn-1-Bu-AZADOH- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide is determined to be 2R,2'S,3aS,7aR.

MeSH terms

Catalysis
Dimerization
Kinetics
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry*
Stereoisomerism
Substrate Specificity

Substances

Spiro Compounds
idesolide