Synthesis 2006(7): 1057-1076  
DOI: 10.1055/s-2006-926376
REVIEW
© Georg Thieme Verlag Stuttgart · New York

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

Stephen Hanessian*, Simon Giroux, Vincent Mascitti
Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec, H3C 3J7, Canada
Fax: +1(514)3435728; e-Mail: stephen.hanessian@umontreal.ca;
Further Information

Publication History

Received 4 October 2005
Publication Date:
08 March 2006 (online)

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

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Both enantiomers of 2-methyl-3-hydroxymethyl propionic acid are available commercially.