A -Capnellene-8p,10a-diol

Pattenden and Teague have prepared tricyclic diol 684 which is epimeric to the naturally occurring A < -capnellene-8p,10a-diol (68S) Their strategy, which is summarized in Scheme LXXI, encompasses two critical cyclization steps. The first is the Lewis acid-catalyzed ring closure of enol acetate 686 and the second involves reductive closure of acetylenic ketone 687. It is of interest that the oxidation of 688 proved to be stereospecific. 

Pattenden, G. and Teague, S.J. (1988) Total synthesis of ( )-A -capnellene-8p,10a-diol./. Chem. Soc. Perkin Trans. 1,1077-1083. 

Gambacorta, A., Fabrizi, G., and Bovicelli, P. (1992) Bicyclo[3.3.1] nonane approach to triquinanes formal synthesis of ( )-A capnellene and ( )-A capnellene-8P-10a-diol. Tetrahedron, 48, 4459-4464. 

---