New approach to bicyclo[5.3.0]decanes: stereoselective guaiane synthesis.
[reaction: see text] A conceptually new and highly versatile approach to bicyclo[5.3.0]decanes, based on dichloroketene cycloaddition-diazoalkane ring expansion, is disclosed, and its relevance to natural product synthesis is demonstrated through the preparation of three guaiane sesquiterpenes. A concise total synthesis of a guaian-8,12-olide, 6-deoxygeigerin, highlights the effectiveness of the new methodology.
Chimie Recherche (LEDSS), Université Joseph Fourier, BP 53, 38041 Grenoble, France.
Yoann
Y
Coquerel
Andrew E
AE
Greene
Jean-Pierre
JP
Deprés