16736-51-9Relevant academic research and scientific papers
An improved synthesis of rhinocerotinoic acid
Gray, Christopher A.,Davies-Coleman, Michael T.,Rivett, Douglas E. A.
, p. 165 - 173 (2003)
The stereoselective synthesis of E-rhinocerotinoic acid has been achieved in five steps from (-)-sclareol in an overall yield of 32%. This constitutes a significant improvement on the previous synthesis of this anti-inflammatory compound.
Synthesis of a Novel Diterpenoid Rearrangement Product
Bendall, Justin G.,Cambie, Richard C.,Moratti, Stephen C.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 1747 - 1756 (1995)
The two intermediates postulated in the rearrangement of the labdane diterpenoid octahydronaphthopyranone (2) into the octahydronaphthofuranone (4) have been synthesized and coupled, thereby providing support for a previously proposed rearrangement mechanism.
Degradation of the side chain of (-)-sclareol: A very short synthesis of nor-ambreinolide and ambrox
Barrero,Alvarez-Manzaneda,Chahboun,Arteaga
, p. 3631 - 3643 (2007/10/03)
The synthesis of nor-Ambreinolide (8) from (-)-sclareol (1) was carried out by treatment with KMnO4-Ac2O and further alkaline hydrolysis. 8 was directly transformed into (-)-ambrox (11) by reduction with metal borohydride in the presence of Lewis acids.
Oxidative degradation of the sclareol side chain: hemisyntheses of ambergris derivatives using in the key steps palladium complexes or ruthenium tetroxide generated in situ
Zahra, Jean-Pierre,Chauvet, Frederic,Coste-Maniere, Ivan,Martres, Paul,Perfetti, Patricia,Waegell, Bernard
, p. 1001 - 1024 (2007/10/03)
We report the hemisyntheses of various ambergris-type derivatives: ambraoxide 4, Ambrox 8, 13-methylambraoxide 13, ambraketal 14, norambraketal 15, non-norambraketal 16 and dioxepane 53.Sclareol 12 is used as starting material because it is currently available from Salvia sclarea.The key steps involve an oxidative degradation of the sclareol 12 side chain, using either palladium complexes or ruthenium tetroxide generated in situ. - Keywords: sclareol; Ambrox; ambraoxide; 13-methylambraoxide; ambraketal; norambraketal; nor-norambraketal; farnesylic aldehyde; palladium complex; ruthenium tetroxide generated in situ; oxidative degradation
INVESTIGATION OF THE PRODUCTS OF THE OZONOLYSIS OF NEOABIENOLS
Koltsa, M. N.,Mironov, G. N.,Aryku, A. N.,Vlad, P. F.
, p. 36 - 42 (2007/10/02)
The ozonolysis of a mixture of 13Z- and 13E-neoabienols (I and III) leads, depending on the conditions, either to 8α-hydroxy-14,15-bis-norlabd-11-en-13-one (IV) or to 8α-hydroxdriman-11-oic acid (VI) or to driman-8α,11-diol (VII).Compound (IV) undergoes hydrogenation smoothly with the formation of a mixture of 8α-hydroxy-14,15-bisnorlabdan-13-one (X) and "sclareol oxide" (XI).
