Bioinspired enantioselective total syntheses of antibacterial callistrilones enabled by double SN2′ cascade

A bioinspired, catalytic approach to the enantioselective total syntheses of antibacterial callistrilones A, C-E and 13-epi-callistrilone E natural products containing an unprecedented, sterically compact [1]benzofuro-[2,3-a]xanthene 6/6/6/5/6/3-fused hexacyclic skeleton is described. The key featur...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-05, Vol.58 (36), p.5474-5477
Main Authors: Dethe, Dattatraya H, Dherange, Balu D, Das, Saikat, Srivastava, Aparna
Format: Article
Language:English
Subjects:
Antiinfectives and antibacterials
Cascade chemical reactions
Enantiomers
Lewis acid
Natural products
Stereoselectivity
Online Access:Get full text
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Summary:A bioinspired, catalytic approach to the enantioselective total syntheses of antibacterial callistrilones A, C-E and 13-epi-callistrilone E natural products containing an unprecedented, sterically compact [1]benzofuro-[2,3-a]xanthene 6/6/6/5/6/3-fused hexacyclic skeleton is described. The key features of the synthesis include a highly regio- and diastereoselective double SN2′ cascade reaction, Lewis acid catalysed Michael addition and late stage diastereoselective epoxide formation from the sterically hindered β-face of the alkene as the key steps.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01398c