Stereocontrolled Synthesis of Carbon Chains Bearing Contiguous Methyl Groups by Iterative Boronic Ester Homologations: Application to the Total Synthesis of (+)-Faranal

Guillaume Dutheuil, Matthew R. Webster, Paul A. Worthington, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

62 Citations (Scopus)
317 Downloads (Pure)

Abstract

Carbon chains bearing 1, 3, 5… n polymethyl groups are ubiquitous in natural products. Recently, effective solutions for a flexible, stereocontolled synthesis of such arrays have been achieved by the groups of Feringa-Minnaard,1 Breidt,2 and Negishi.3 Carbon chains bearing adjacent methyl groups, although less common, are also frequently encountered4 (Figure 1), but a general stereocontrolled solution to this problem has not been advanced.5 For example, in the previous syntheses of the insect pheromone (+)-faranal (1),5b one or both methyl groups originate from a carboxylic ester to enable control of relative stereochemistry during C[BOND]C bond formation (both utilize resolution to achieve absolute control).6 Introducing the methyl groups in the wrong oxidation state invariably leads to an increase in the total number of steps required.
Original languageEnglish
Pages (from-to)6317-6319
Number of pages3
JournalAngewandte Chemie - International Edition
Volume48
Issue number34
Early online date13 May 2009
DOIs
Publication statusPublished - 10 Aug 2009

Keywords

  • boronic esters
  • C-C coupling
  • lithiated carbamates
  • natural products
  • CATALYTIC ASYMMETRIC-SYNTHESIS
  • OPTICALLY-ACTIVE FORMS
  • TRAIL PHEROMONE
  • PHARAOHS ANT
  • GRIGNARD-REAGENTS
  • (+)-SPARTEINE SURROGATE
  • CONJUGATE ADDITION
  • SECONDARY ALCOHOLS
  • CHIRAL CARBENOIDS
  • ROUTE

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