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New Approach to Bicyclo[5.3.0]decanes: Stereoselective Guaiane Synthesis

✍ Scribed by Coquerel, Yoann; Greene, Andrew E.; Deprés, Jean-Pierre

Book ID
127317845
Publisher
American Chemical Society
Year
2003
Tongue
English
Weight
61 KB
Volume
5
Category
Article
ISSN
1523-7060

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✍ Jalluri S Ravi Kumar; Michael F O'Sullivan; Sarah E Reisman; Catherine A Hulford 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 92 KB

An efficient strategy for the rapid construction of the guiane bicyclo[5.3.0]decane ring system from appropriately substituted 4-alkyn-1-ols has been developed. This methodology relies on a MeLi-catalyzed tandem 5-exo-dig cyclization/Claisen rearrangement sequence as the key ring forming step.