Total synthesis of (-)-haouamine B pentaacetate and structural revision of haouamine B

Yuichi Momoi; Kei-ichiro Okuyama; Hiroki Toya; Kenji Sugimoto; Kentaro Okano; Hidetoshi Tokuyama

doi:10.1002/anie.201407686

Total synthesis of (-)-haouamine B pentaacetate and structural revision of haouamine B

Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13215-9. doi: 10.1002/anie.201407686. Epub 2014 Oct 5.

Authors

Yuichi Momoi¹, Kei-ichiro Okuyama, Hiroki Toya, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba, Aramaki, Aoba-ku, Sendai 980-8578 (Japan).

PMID: 25284461
DOI: 10.1002/anie.201407686

Abstract

The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía.

Keywords: alkaloids; aromatic substitution; cross-coupling; cyclization; total synthesis.

Publication types

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

MeSH terms

Cyclization
Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
Molecular Structure
Stereoisomerism

Substances

Heterocyclic Compounds, 4 or More Rings
haouamine B