Approaches to the Total Synthesis of Calycotomine, a Widespread 1-Hydroxymethyl-Substituted Simple Tetrahydroisoquinoline

Teodoro S. Kaufman

doi:10.1055/s-2005-861793

REVIEW

Approaches to the Total Synthesis of Calycotomine, a Widespread 1-Hydroxymethyl-Substituted Simple Tetrahydroisoquinoline

Teodoro S. Kaufman*
Instituto de Química Orgánica de Síntesis -IQUIOS- (CONICET-UNR) and Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, S2002LRK Rosario, República Argentina
Fax: +54(341)4370477; e-Mail: tkaufman@fbioyf.unr.edu.ar;

Abstract

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Abstract

1-Hydroxymethyl-substituted tetrahydroisoquinolines are scarce in nature; the widespread alkaloid calycotomine is its most prominent example. The different total syntheses of this natural product, used as test ground for the development of novel synthetic methodologies during the last forty years, and those of some structurally related precursors, are reviewed.

1 Introduction
2 Bischler-Napieralski Cyclization
3 Pictet-Spengler Condensation
4 Asymmetric Intramolecular Allylic Amination
5 Bobbitt Isoquinoline Synthesis
6 Syntheses of Calycotomine from Preformed Isoquinolines
7 Intramolecular Ring-Opening of a Chiral 1,3-Perhydrobenzoxazine
8 Conclusions

Key words

natural products - total synthesis - alkaloids - cyclizations - calycotomine

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