A ring-closing metathesis approach to the bicyclo[4.3.1]decane core of caryolanes

作者：Goldring William P D^*; Paden Warren T

来源：Tetrahedron Letters, 2011, 52(8): 859-862.

DOI：10.1016/j.tetlet.2010.11.138

• Caryolane
• Ring-closing metathesis
• Bicyclic ring systems
• Cyclohexenone

A synthesis of highly substituted and sterically congested bicyclo[4.3.1]decenes, a structure embedded in the core 4,7,6-tricyclic system of natural caryolanes, was successfully achieved via a ring-closing metathesis (RCM) reaction of syn-1,3-diene substituted cyclohexanols. The construction of the diene substrates, starting from 4-acetoxy-3-methyl-2-cyclohexen-1-one, employed diastereoselective copper-mediated conjugate addition and Grignard reactions. An X-ray crystal structure determination of a key synthetic intermediate confirmed the relative stereochemistry of the RCM bicyclic product.

• 出版日期2011-2-23