TY  - JOUR
A1  - Schultze, Christiane
A1  - Schmidt, Bernd
T1  - Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins
T2  - Beilstein journal of organic chemistry
N2  - 8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing olefin metathesis (RCM). Furano-, pyrano-, oxepino- and azepinocoumarins were synthesized from the same set of precursors using Ru-catalyzed double bond isomerizations and RCM in a defined order. One class of products, pyrano[2,3-f]chromene-2,8-diones, were inaccessible through direct RCM of an acrylate, but became available from the analogous allyl ether via an assisted tandem catalytic RCM/allylic oxidation sequence.
KW  - coumarins
KW  - heterocycles
KW  - isomerization
KW  - olefin metathesis
KW  - ruthenium
Y1  - 2018
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/48669
SN  - 1860-5397
VL  - 14
SP  - 2991
EP  - 2998
PB  - Beilstein-Institut zur Förderung der Chemischen Wissenschaften
CY  - Frankfurt, Main
ER  -