Diversity-Oriented Synthesis of Natural Products via Gold-Catalyzed Cascade Reactions

Abstract

This account describes our group’s latest research in the field of diversity-oriented synthesis of natural products via gold-catalyzed cascade reactions. We present two general strategies based on gold-catalyzed cycloisomerization: a gold-catalyzed cascade reaction of 1,7-diynes and a pinacol-terminated gold-catalyzed cascade reaction. We highlight our development of synthetic methods for the construction of biologically active natural products by using these two strategies.

1 Introduction

2 Gold-Catalyzed Cascade Reactions of 1,7-Diynes

2.1 Collective Synthesis of C15 Oxygenated Drimane-Type Sesquiterpenoids

2.2 Synthesis of Left-Wing Fragment of Azadirachtin I

2.3 Collective Synthesis of Cladiellins

3 Pinacol-Terminated Gold-Catalyzed Cascade Reaction

3.1 Asymmetric Formal Total Synthesis of (+)-Cortistatins

3.2 Total Synthesis of Orientalol F

3.3 Asymmetric Total Synthesis of (–)-Farnesiferol C

4 Summary and Outlook

Key words

gold catalysis - natural products - cascade reaction - total synthesis

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