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Rapid Access to Benzofuran‐Based Natural Products through a Concise Synthetic Strategy
Author(s) -
Rao Maddali L. N.,
Murty Venneti N.
Publication year - 2016
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.201600154
Subject(s) - benzofuran , chemistry , domino , reagent , combinatorial chemistry , total synthesis , organic chemistry , stereochemistry , catalysis
A concise strategy is described for the synthesis of ailanthoidol ( 1 ), egonol ( 2 ), homoegonol ( 3 ), demethoxyegonol ( 4 ), demethoxyhomoegonol ( 5 ), and stemofuran A ( 6 ). This approach involves a Pd‐catalysed domino cyclization/coupling process using triarylbismuth reagents for the generation of the benzofuran core. Subsequent structural modifications then give the final targets. The high yielding synthesis of the recently isolated natural products egonol‐9( Z )‐12( Z )‐linoleate ( 2a ), 7‐demethoxyegonol‐9( Z )‐12( Z )‐linoleate ( 4a ), and 7‐demethoxy‐egonol‐9( Z )‐oleate ( 4b ) are also reported.