Synthesis 2017; 49(02): 237-251
DOI: 10.1055/s-0035-1562540
short review
© Georg Thieme Verlag Stuttgart · New York

Strategies for the Synthesis of Deoxypropionates

Fabian Schmid, Angelika Baro, Sabine Laschat*
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Publikationsverlauf

Received: 15. Juli 2016

Accepted: 22. Juli 2016

Publikationsdatum:
09.September 2016 (eFirst)

Dedicated to Professor Dieter Enders on the occasion of his 70th birthday

Abstract

Deoxypropionates constitute an important class of polyketide natural products. The biological properties of deoxypropionates are diverse and synthetic strategies toward their preparation are equally manifold. This short review presents some recent developments on the synthesis of deoxypropionate units involving, besides iterative and non-iterative routes, other methods such as stereoselective Mukaiyama reactions or lithiation–borylation–protodeboronation sequences.

1 Introduction

2 Biosynthesis of Deoxypropionates

3 Iterative Synthetic Methods

3.1 Conjugate Addition of Cuprates

3.2 Copper-Catalyzed Conjugate Additions

3.3 Copper-Mediated Allylic Substitution

3.4 Myers Alkylation

3.5 Zirconium-Catalyzed Carboalumination

3.6 Homologation of Boronates with Organolithiums

4 Non-Iterative Methods

4.1 Enzymatic Desymmetrization

4.2 Ex Chiral Pool Synthesis from Wax Esters

4.3 Ex Chiral Pool Synthesis from the Roche Ester

4.4 Sequential [3,3]-Sigmatropic Rearrangement and Catalytic Hydrogenation

5 Miscellaneous Methods

6 Conclusion