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Synthesis of isochromene derivatives using an intramolecular benzylic C(sp(3))-C(sp(2)) bond forming Heck reaction on vinylogous carbonates

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Title Synthesis of isochromene derivatives using an intramolecular benzylic C(sp(3))-C(sp(2)) bond forming Heck reaction on vinylogous carbonates
 
Creator GHARPURE, SJ
SHELKE, YG
REDDY, SRB
 
Subject STEREOSELECTIVE CONSTRUCTION
PALLADIUM
HALIDES
CYCLIZATION
OLEFINS
ROUTE
1H-ISOCHROMENES
ELECTROPHILES
ANTIBIOTICS
LACTONES
 
Description An intramolecular, benzylic C(sp(3))-C(sp(2)) bond forming Heck reaction on vinylogous carbonates (or beta-alkoxyacrylates) is developed for an efficient synthesis of isochromene derivatives. A competitive Heck reaction between a normal olefin and a vinylogous carbonate moiety led to a dihydronaphthalene product via coupling with olefin exclusively. The method was used in the synthesis of a core of cis-dihydrokalafungin and monocerolide.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-12-29T06:14:32Z
2014-12-29T06:14:32Z
2014
 
Type Article
 
Identifier RSC ADVANCES, 4(87)46962-46965
2046-2069
http://dx.doi.org/10.1039/c4ra08421g
http://dspace.library.iitb.ac.in/jspui/handle/100/17284
 
Language English