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Facile approach to the bicyclo[5.3.0]decane ring system; efficient synthesis of (±)-7-epi-β-bulnesene

✍ Scribed by Jalluri S Ravi Kumar; Michael F O'Sullivan; Sarah E Reisman; Catherine A Hulford; Timo V Ovaska

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
92 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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An enantioselective method to prepare trans-fused bicyclo[5.3.0]decane systems is described. This methodology is based on two key reactions: a [4ϩ3] cycloaddition reaction (to generate the seven-membered ring) and the Nicholas reaction (to insert the five-membered ring). The application of this meth

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