643-52-7Relevant articles and documents
Titanium-catalyzed enantioselective synthesis of α-ambrinol
Justicia, Jose,Campan, Araceli G.,Bazdi, Btissam,Robles, Rafael,Cuerva, Juan M.,Oltra, J. Enrique
experimental part, p. 571 - 576 (2009/05/07)
We describe the first enantioselective synthesis of the odorant compound (-)-α-ambrinol (96% ee) from commercial geranylacetone. The key steps are a Jacobsen's asymmetric epoxidation and a titanium-catalyzed stereoselective cyclization initiated by radical epoxide opening. The oxirane ring opening proceeds with retention of configuration at the epoxide chiral center, giving a secondary alcohol which can be advantageously exploited to raise the ee provided by the synthetic sequence. We also synthesized (+)-α-ambrinol by a closely related procedure, showing the synthetic versatility of combining titanium-catalyzed cyclization with Jacobsen's epoxidation reactions.
New Synthesis of γ-Homocyclogeranial, γ-Dihydroionone and Their Derivatives
Kawanobe, Tsuneo,Kogami, Kunio,Hayashi, Kazuo,Matsui, Masanao
, p. 461 - 464 (2007/10/02)
A new and efficient synthesis of γ-homocyclogeranial (4), γ-dihydroionone (3) and their derivatives, 5, 6, 7 and 8, volatile components of ambergris, is described.Their compounds were synthesized via Claisen rearrangement of (3,3-dimethylcyclohexenyl)methyl vinyl ether (14).
