Synlett 2021; 32(05): 436-446
DOI: 10.1055/s-0040-1707144
account
The Power of Transition Metals: An Unending Well-Spring of New Reactivity

Total Syntheses of Cylindrocyclophanes Exemplifying the Power of Transition-Metal Catalysis in Natural-Product Synthesis

Dino Berthold
,
D.B. is grateful for a Feodor-Lynen Fellowship from the Alexander von Humboldt Foundation.


Dedicated to Barry Trost on the occasion of his 80th birthday.

Published as part of the Cluster The Power of Transition Metals: An Unending Well-Spring of New Reactivity

Abstract

Cylindrocyclophanes are a class of naturally occurring 22-membered macrocycles with a unique architecture and interesting physical, chemical, and biological properties. This comprehensive account summarizes progress in various synthetic approaches to these compounds during the last twenty years, thereby emphasizing the key steps for establishing the [7,7]-paracyclophane scaffold, as well as alternative approaches to the construction of its stereocenters. Many of these syntheses highlight the power of transition-metal catalysis for natural-product synthesis. Furthermore, the unraveling of the biosynthesis to these natural products in Cylindrospermum licheniforme is discussed.

1 Introduction

2 Biosynthesis

3 Smith’s Synthesis of (–)-Cylindrocyclophanes A and F

4 Hoye’s Synthesis of (–)-Cylindrocyclophane A

5 Iwabuchi’s Syntheses of (–)-Cylindrocyclophane A and (+)-Cylindrocyclophane A

6 Nicolaou’s Synthesis of (–)-Cylindrocyclophanes A and F

7 Breit’s Synthesis of (–)-Cylindrocyclophane F

8 Conclusion



Publication History

Received: 03 May 2020

Accepted: 15 May 2020

Publication Date:
18 June 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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