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
Key words
deoxypropionates - polypropionates - polyketides - natural products - total synthesis
- stereoselective synthesis
