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Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins.


ABSTRACT: 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.

SUBMITTER: Schultze C 

PROVIDER: S-EPMC6296409 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins.

Schultze Christiane C   Schmidt Bernd B  

Beilstein journal of organic chemistry 20181205


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-<i>f</i>]chromene-2  ...[more]

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