Asymmetric synthesis of penostatins A-D from -ascorbic acid

The first asymmetric synthesis of (−)-penostatins B and D and the practical synthesis of (+)-penostatins A and C have been accomplished through a flexible strategy. The features of the synthesis are a BF 3 ·OEt 2 -mediated Diels-Alder reaction of chiral dienophiles and methylcyclopentadienes with hi...

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Published in:Organic & biomolecular chemistry 2024-09, Vol.22 (37), p.7649-7658
Main Authors: Wang, Maolin, Jia, Yuanliang, Wu, Folei, Li, Zupei, Shao, Lijun, Chen, Xiaochuan
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Summary:The first asymmetric synthesis of (−)-penostatins B and D and the practical synthesis of (+)-penostatins A and C have been accomplished through a flexible strategy. The features of the synthesis are a BF 3 ·OEt 2 -mediated Diels-Alder reaction of chiral dienophiles and methylcyclopentadienes with high chemo-, regio-, and stereoselectivity, followed by ozonolysis to install the common trisubstituted cyclopentane intermediate, and a hetero-Diels-Alder reaction with easily tunable facial selectivity, followed by sulfonate elimination to construct both enantiomeric tricyclic systems for penostatins A/C and B/D, respectively. The asymmetric synthesis of penostatins A-D are achieved through a flexible strategy based on an intramolecular oxa-Diels-Alder reaction with tunable facial stereoselectivity.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob01186d