A convenient synthesis of trans-sabinene hydrate from (-)-3-thujol via a highly selective ene reaction of singlet oxygen

Article abstract of DOI:10.1016/0968-0896(96)00020-X

trans-Sabinene hydrate (1), was synthesized from (-)-3-thujol (2) in four steps. The key step was the selective formation of trans-2-hydroxy-3-thujene (6) by photooxygenation of a 3:1 mixture of 2- and 3-thujenes (4 and 5) obtained from (-)-3-thujol mesylate (3). Hydrogenation of 6 gave compound 1 in 46% overall yield.