Cover Picture: Total Synthesis and Olfactory Evaluation of (1R*,3S*,6S*,7S*,8S*)‐3‐Hydroxy‐6,8‐dimethyltricyclo[5.3.1.03,8]undecan‐2‐one: A New Synthetic Route to the Patchoulol Skeleton (Eur. J. Org. Chem. 6/2006)

Abstract

AbstractThe cover picture shows the ketol soaring above the navel of an oriental belly dancer, which smells not “like teen spirit” but actually like patchouli. This is symbolized by the colors the sunlight is refracted into, the colors of the cashmere fabrics with which patchouli leaves first came to Europe. As bifunctional compounds of these molecular dimensions were known to be odorless, the pronounced patchouli odor is indeed very surprising. This ketol is a superstructure of (−)‐patchoulol and a recently discovered high‐impact spirocyclic patchouli odorant, and its odor proves this superposition analysis to be valid. Its total synthesis was accomplished in 13 steps with a total yield of 7% from the inexpensive commercial odorant Cyclal C, and features a novel intramolecular Prins reaction. This unusual access to the tricyclic homoisotwistane skeleton constitutes, in addition, a new formal total synthesis of patchoulol. All details are discussed in the article by P. Kraft et al. on p. 1403 ff.