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Domino Hydroalkoxylation‐[4+2]‐Cycloaddition for Stereoselective Synthesis of 1,4‐Heterocycle‐Fused Chromenes: Rapid Access to the [6‐6‐7‐6] Tetracyclic Core of Cytorhizhins B–D
Author(s) -
Gharpure Santosh J.,
Nanda Santosh K.,
Fartade Dipak J.,
Vishwakarma Dharmendra S.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901565
Subject(s) - stereoselectivity , chemistry , domino , cycloaddition , cascade reaction , stereochemistry , combinatorial chemistry , catalysis , organic chemistry
A substrate dependent regio‐ and stereoselective domino hydroalkoxylation‐formal‐[4+2] cycloaddition is described for the facile synthesis of linear as well as spirocyclic 1,4‐heterocycle‐fused chromene ketals. Enantiospecific synthesis of oxazepino chromene derivatives was successfully carried out using chiral pool amino alkynols. The developed hydroalkoxylation cascade offered rapid access to the spirocyclic [6‐6‐7‐6] tetracyclic core of cytorhizhins B–D with correct relative configuration.