Synthesis 2016; 48(11): 1573-1596
DOI: 10.1055/s-0035-1560431
review
© Georg Thieme Verlag Stuttgart · New York

Carbonylations of Alkenes in the Total Synthesis of Natural Compounds

Paul H. Gehrtz
,
Vera Hirschbeck
,
Benjamin Ciszek
,
Ivana Fleischer*
Further Information

Publication History

Received: 05 February 2016

Accepted after revision: 04 March 2016

Publication Date:
31 March 2016 (online)


Abstract

The goal of this review is to highlight the applications of carbonylation reactions of alkenes in the total synthesis of natural compounds. These highly atom-economic reactions, which are known for their industrial applications, constitute attractive synthetic methodologies for the selective construction of carbonyl compounds. We aimed at the selection of recent methodologically attractive syntheses where carbonylations were applied as key steps. In addition, a few examples of the related carbonylation of allenes are shown.

1 Introduction

2 Hydroformylation

3 Hydroaminomethylation and Related Tandem Hydroformylation Reactions

4 Reppe Carbonylation

5 Allylic Carbonylation

6 Oxidative Carbonylation

7 Pauson–Khand Reaction

8 Summary and Outlook