A novel and concise synthesis of spirodienone alkaloids using hypervalent iodine(III) reagents

Hiromi Hamamoto; Yukiko Shiozaki; Kayoko Hata; Hirofumi Tohma; Yasuyuki Kita

doi:10.1248/cpb.52.1231

A novel and concise synthesis of spirodienone alkaloids using hypervalent iodine(III) reagents

Chem Pharm Bull (Tokyo). 2004 Oct;52(10):1231-4. doi: 10.1248/cpb.52.1231.

Authors

Hiromi Hamamoto¹, Yukiko Shiozaki, Kayoko Hata, Hirofumi Tohma, Yasuyuki Kita

Affiliation

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

PMID: 15467242
DOI: 10.1248/cpb.52.1231

Abstract

Intramolecular oxidative coupling reaction of N-protected benzyltetrahydroisoquinoline derivatives using hypervalent iodine(III) reagents was investigated. The use of remarkable combination of phenyliodine bis (trifluoroacetate) (PIFA) and heteropoly acid (HPA) in wet acetonitrile smoothly afforded morphinandienone alkaloids, while neospirinedienone alkaloids were obtained in high yield under anhydrous conditions.

Publication types

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

MeSH terms

Acetonitriles
Alkaloids / chemical synthesis*
Catalysis
Indicators and Reagents / chemistry
Molecular Structure
Morphinans / chemistry
Oxidation-Reduction
Spiro Compounds / chemical synthesis*
Tetrahydroisoquinolines / chemistry*

Substances

Acetonitriles
Alkaloids
Indicators and Reagents
Morphinans
Spiro Compounds
Tetrahydroisoquinolines
acetonitrile