Synthesis 2024; 56(01): 161-170
Iterative Assembly of Chiral Alcohols Utilizing CMMP-Mediated Mitsunobu Reactions
,
Saki Ise
,
Tetsuto Tsunoda
,
Hiroto Kaku∗
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.
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 -
desulfonylation
Supporting 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
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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