Aza-Annulation Strategies in Alkaloid Total Synthesis

Adrien K. Lawrence; Karl Gademann

doi:10.1055/s-2008-1032134

REVIEW

Aza-Annulation Strategies in Alkaloid Total Synthesis

Adrien K. Lawrence, Karl Gademann*
Chemical Synthesis Laboratory, Swiss Federal Institute of Technology (EPFL), SB-ISIC-LSYNC, 1015 Lausanne, Switzerland
Fax: +41(21)6939700; e-Mail: karl.gademann@epfl.ch;

Abstract

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Abstract

This review highlights the synthesis of nitrogen-containing natural products via aza-annulation. Strategic, tactical, and methodological perspectives are discussed, including recent developments such as metal- or organocatalyzed reactions, oxidative or reductive cyclizations, biomimetic processes, cascade reactions, and cycloadditions. Such key steps are presented in the context of the total syntheses of tropinone, batzelladine, lyconadin, FR901483, strychnofoline, discorhabdin, necatarone, aspidophytine, dibromophakellstatin, anachelin, the acridones, alkaloid GB13, cephalotaxine, strychnine, setoclavine, porantherine, vallesamine, nitraramine, cylindricine, the daphniphyllines, symbiomime, alstonerine, tangutorine and flustramine.

1 Introduction

2 Aza-Annulation Reactions

3 Conclusion

Key words

biomimetic synthesis - cyclizations - natural products - stereoselective synthesis - total synthesis

Full Text

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