Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 30, Pages 6618-6622Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob00974e
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Funding
- CSIR-New Delhi, India (INPROTICS-Pharma and Agro) [HCP0011, 9/1/CS/CIA/2017-MD]
- CSIR-India
- UGC-India
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This method utilizes an unprecedented intramolecular cascade strategy to construct alpha, beta-unsaturated oxaspirolactones, using pi-electrophilic Lewis acid-catalyzed cyclization, spirolactonization steps, and semi-protected substrates can also produce oxaspirolactones under optimal reaction conditions.
Herein we disclose an unprecedented intramolecular cascade strategy for the construction of alpha,beta-unsaturated [5,5]- and [6,5]-oxaspirolactones that capitalizes on the pi-electrophilic Lewis acid-catalyzed 5-exo-dig or 6-exo-dig mode of cyclization of propargylic diol esters, followed by dehydration and spirolactonization steps. Moreover, semi-protected substrates also delivered the respective oxaspirolactones with the same ease and in appreciable yields under optimal reaction conditions.
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