Projects per year
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 language | English |
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Pages (from-to) | 896-902 |
Number of pages | 7 |
Journal | Nature Chemistry |
Volume | 9 |
Issue number | 9 |
Early online date | 10 Apr 2017 |
DOIs | |
Publication status | Published - 1 Sept 2017 |
Keywords
- Synthetic chemistry methodology
- Stereochemistry
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Dive into the research topics of 'Iterative assembly line synthesis of polypropionates with full stereocontrol'. Together they form a unique fingerprint.Projects
- 4 Finished
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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research
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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P. (Principal Investigator)
28/02/14 → 29/11/17
Project: Research
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Profiles
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Professor Varinder K Aggarwal
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
Person: Academic