Abstract
A total synthesis is presented for himachalene-related norsesquiterpene ketone 1 (racemic), based on the Robinson annulation and other standard reactions. The route involved five steps from cycloheptanone. A favorable result was that the desired diastereomer of 1 was obtained preferentially (97:3) over the unwanted one. Molecular modeling (ab initio calculations) aided in confirming the assignment of relative stereochemistry of 1 and in rationalizing the observed ratio of diastereomers. Three related sesquiterpene hydrocarbons and two alcohols were subsequently produced from 1. The six compounds occur naturally in several flea beetle species and likely serve a pheromonal function.
Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
