Novel rearrangement of 2-α-isopropyl-8-oxabicyclo[3.2.1]oct-6-ene producing the monoterpene 3-hydroxyphellandral
Abstract
We describe a five-step synthesis of 2-α-isopropyl-8-oxabicyclo[3.2.1]oct-6-ene from 1,1,3, 3-tetrabromo-4-methylpentan-2-one, and its unexpected rearrangement to yield trans-3- hydroxy-4-isopropylcyclohex-1-enecarbaldehyde (3-hydroxyphellandral).