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Synthesis of ‘inside–outside’ medium-sized rings via ring-closing metathesis

✍ Scribed by Marie E Krafft; Y.Y Cheung; Sean A Kerrigan; Khalil A Abboud

Book ID
104252732
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
493 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Functionalized and unfunctionalized dienes were synthesized from lactones 7 and 6, respectively, which were subjected to ring-closing metathesis (RCM) using Grubbs' catalysts. These dienes provide a systematic study of the stereochemical requirements for efficient cyclization. Moreover, it has been established that, within a uniquely defined oxabicyclo[3.3.0]octane template, medium sized rings bearing an 'in-out' intrabridgehead stereochemical relationship can been synthesized in good yield.

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