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Optical stability of a nine-membered ring bridged biphenyl

โœ Scribed by Kurt Mislow; Seymour Hyden; Hans Schaefer

Book ID
104234989
Publisher
Elsevier Science
Year
1961
Tongue
French
Weight
195 KB
Volume
2
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

THE stereochemistry of 1,2,3,4-dibenzcy~ionona-I,3-diene-~-carboxylic acid (I) is of considerable interest for several reasons.

A nine-membered ring bridged biphenyl No.12 conveniently prepared from IIa by LiAlH4 reduction of the ethyl ester to IId,

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Synthesis of bridged nine-membered ring
Synthesis of bridged nine-membered ring ethers: Studies directed towards the synthesis of eunicellin-based marine diterpenes
โœ M. Nowakowski; H.M.R. Hoffmann ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 410 KB

A concise annulation-fragmentation strategy has been elaborated for the construction of the bridged nine-membered ring ether moiety of the eunicelline diterpenes. Key steps are a SmI:-induced Barbier cyclization and an oxidative ring fission using cerium(IV) ammonium nitrate (CAN)