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DOI: 10.1055/a-2175-1271
Iterative Assembly of Chiral Alcohols Utilizing CMMP-Mediated Mitsunobu Reactions
This work was supported by Grants-in-Aid from the JSPS KAKENHI (20K06955 and 23K06062) and Mitsubishi Tanabe Pharma Award in Synthetic Organic Chemistry, Japan.
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Abstract
An iterative assembly of chiral alcohol building blocks is reported utilizing cyanomethylene trimethylphosphorane (CMMP)-mediated Mitsunobu reactions. 1,3-Benzodithiole tetraoxide (BDT) was used as the platform to prepare long-chain saturated compounds with multiple stereocenters en route to polyisoprenoid natural products. Selectively protected chiral 1,3-butanediols played a key role in iterative chain elongation for the construction of 1,5-dimethyl branched arrays with high stereocontrol.
Key words
Mitsunobu reaction - BDT - chiral alcohols - stereochemistry - polyisoprenoids - CMMP - desulfonylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2175-1271.
- Supporting Information
Publication History
Received: 13 August 2023
Accepted after revision: 13 September 2023
Accepted Manuscript online:
13 September 2023
Article published online:
26 October 2023
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