The Oxa-Pictet-Spengler Cyclization: Synthesis of Isochromans and Related Pyran-Type Heterocycles

Enrique L. Larghi; Teodoro S. Kaufman

doi:10.1055/s-2005-918502

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Synthesis 2006(2): 187-220
DOI: 10.1055/s-2005-918502

REVIEW

The Oxa-Pictet-Spengler Cyclization: Synthesis of Isochromans and Related Pyran-Type Heterocycles

Enrique L. Larghi, 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;

Further Information

Publication History

Received 29 June 2005
Publication Date:
21 December 2005 (online)

Abstract
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Abstract

Compounds bearing the isochroman ring system are found in natural and synthetic products of interest. The oxa-Pictet-Spengler condensation is a valuable tool for the preparation of polysubstituted isochromans and related oxygen-bearing heterocycles. The different stagings of the oxa-Pictet-Spengler reaction, as well as the scope and limitations of this transformation, are discussed.

1 Introduction
2 Intermolecular Oxa-Pictet-Spengler Condensation
2.1 Synthesis of 1-Substituted Isochromans
2.2 Synthesis of 1,1-Disubstituted Isochromans
2.3 Diastereoselective Synthesis of 1,3-Disubstituted Isochromans
2.4 Synthesis of 3-Substituted Isochromans
2.5 Synthesis of C-4 Substituted Isochroman Derivatives
3 Intramolecular Oxa-Pictet-Spengler Cyclizations
3.1 Synthesis of 1-Substituted Isochromans
3.2 Diastereoselective Synthesis of 1,3-Disubstituted Isochromans
3.3 Synthesis of 1,3,4-Trisubstituted Isochromans
4 The Oxa-Pictet-Spengler Condensation in the Absence of Acid Catalysts
5 Naturally Occurring Oxa-Pictet-Spengler Cyclizations
6 Oxa-Pictet-Spengler Reactions towards Optically Active Compounds
7 Synthesis of Heterocycles other than Isochroman Derivatives
8 Conclusions

Key words

oxa-Pictet-Spengler - cyclization - isochromans - natural products - chemical synthesis

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