The Iterative Synthesis of Acyclic Deoxypropionate Units and Their Implication­ in Polyketide-Derived Natural Products

Abstract

Interest in natural products containing deoxypropionate units has recently grown since the emergence of powerful synthetic strategies to access syn and anti stereoarrays. The purpose of this review is to focus on iterative methodologies leading to enantiopure carbon chains harboring two or more contiguous deoxypropionate units.

• 1 Introduction

• 2 Chiral Auxiliary Mediated Methods

• 2.1 1,4-Conjugate Additions

• 2.2 Enolate and Azaenolate Alkylations

• 3 Asymmetric Allylic Substitution

• 4 Nonchiral Auxiliary Mediated Methods

• 4.1 Substrate and Conformational Control

• 4.2 Substrate and Reagent Directed Control

• 5 Indirect Methods

• 6 Catalytic Methods

• 6.1 Zr-Catalyzed Carboalumination Method

• 6.2 Catalytic Organocuprate Addition Method

• 7 Synopsis

natural products - enolates - conjugate additions - conformational analysis

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