Iterative assembly line synthesis of polypropionates with full stereocontrol

Teerawut Bootwicha, Julian M. Feilner, Eddie L. Myers, Varinder K. Aggarwal

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

27 Citations (Scopus)
351 Downloads (Pure)

Abstract

The polypropionate motif is ubiquitous, being characteristic of the most important family of natural products for human health, the polyketides. Numerous strategies have been devised to construct these molecules with high stereocontrol, but certain stereoisomers remain challenging to prepare. We now describe the development of an iterative assembly line strategy for the construction of polypropionates. An assembly line strategy for the synthesis of deoxypolypropionates has already been described. However, the introduction of carbinol units required the development of new building blocks and new reaction conditions. This has been achieved by the use of enantioenriched lithiated α-chlorosilanes [1-((2′-lithiochloromethyldimethylsilyl)-methyl)-2-(methoxymethyl)-pyrrolidine], thus enabling the programmed synthesis of polypropionates in a fully stereocontrolled manner, including the stereochemically challenging anti-anti isomers. The versatility of the approach is exemplified in its extension to the synthesis of 1,3-related polyols. The methodology now allows access to a much wider family of polyketide natural products with stereochemistry being dialled in at will.

Original languageEnglish
Pages (from-to)896-902
Number of pages7
JournalNature Chemistry
Volume9
Issue number9
Early online date10 Apr 2017
DOIs
Publication statusPublished - 1 Sep 2017

Keywords

  • Synthetic chemistry methodology
  • Stereochemistry

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