77239-52-2Relevant academic research and scientific papers
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.
Sesquiterpenoid Constituents of the Liverwort, Ptychanthus striatus (LEHM. et LINDENB.) NEES
Takeda, Reiji,Naoki, Hideo,Iwashita, Takashi,Mizukawa, Kosei,Hirose, Yoshio,et al.
, p. 1125 - 1132 (2007/10/02)
Four sesquiterpenoids, striatene, striatol, β-monocyclonerolidol and ptychanolide, were isolated from the liverwort Ptychanthus striatus (LEHM. et LINDENB.)NEES. Their structures have been established by spectroscopic analysis and chemical transformation. Three of them, striatene, striatol and β-monocyclonerolidol, are interesting in terms of the evolution of the liverwort fom the algae.
STRUCTURAL AND ABSOLUTE CONFIGURATIONAL STUDIES OF STRIATENE, STRIATOL AND β-MONOCYCLONEROLIDOL, THREE SESQUITERPENOIDS FROM THE LIVERWORT PTYCHANTHUS STRIATUS (LEHM. ET LINDBEMB.) NEES
Takeda, Reiji,Mori, Reiko,Hirose, Yoshio
, p. 1625 - 1628 (2007/10/02)
Three new sesquiterpenoids, striatene, striatol and β-monocyclonerolidol, were isolated from the liverwort Ptychanthus striatus (Lehm. et Lindemb.) Nees.Their structures have been established by spectroscopic analysis and chemical transformation.These compounds are interesting in terms of the evolution of the liverwort from algae.
SYNTHESIS OF (+/-)-α-AMBRINOL
Takazawa, Osamu,Tamura, Hiroshi,Kogami, Kunio,Hayashi, Kazuo
, p. 1257 - 1258 (2007/10/02)
Synthesis of α-ambrinol was successfully accomplished by cyclization of dihydro-γ-ionone ethylene acetal which was prepared by the titanium(IV)-promoted reaction of 3,3-dimethyl-1-trimethylsiloxycyclohexene with methyl vinyl ketone ethylene acetal followed by exomethylenation with triphenylphosphonium methylide.
