93860-80-1Relevant academic research and scientific papers
THE CONVERSION OF (-)- AND (+)-DIHYDROCARVONE INTO CHIRAL INTERMEDIATES FOR THE SYNTHESIS OF (-)-POLYGODIAL, (-)-WARBURGANAL AND (-)-MUZIGADIAL
Jansen, Ben. J. M.,Kreuger, Jacoba A.,Groot, Aede De
, p. 1447 - 1452 (1989)
(-)-Dihydrocarvone was converted into (-)-(4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-4a,8,8,trimethylnaphthalene-2(H)-one (1) via an efficient route in which a Wolff-Kishner reduction, accompanied with a double bond isomerisation brought on a major simplification.Ketone 1 is a suitable intermediate for the syntheses of the insectantifeedants (-)-polygodial and (-)-warburganal. (+)-Dihydrocarvone was converted into (+)-(4aR,7S,8aR)-4a,7-dimethyl-8-methylene-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2(1H)-one (2), an intermediate ketone for synthesis of (-)-muzigadial.
The Synthesis of Fenical and Sims' Structure of Cycloeudesmol. Stereospecific Total Syntheses of (+)-7β-(1-Hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene, (+)-7α-(1-Hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene, (+)-7β-(1-Hydr...
Ando, Masayoshi,Sayama, Shinsei,Takase, Kahei
, p. 251 - 264 (2007/10/02)
Stereospecific total syntheses of the four diastereoisomers of Fenical and Sims' structure of cycloeudesmol, (+)-7β-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene (Ia), (+)-7α-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aα-decahydrocyclopropanaphthalene (Ib), (+)-7β-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aβ-decahydrocyclopropanaphthalene (Ic), and (+/-)-7α-(1-hydroxy-1-methylethyl)-4aβ-methyl-1aβ-decahydrocyclopropanaphthalene (Id), were carried out with the object of establishing the structure of cycloeudesmol.The key step of these syntheses involves the Simmons-Smith reaction directed by the hydroxyl group at the allylic position or the homoallylic position.
An Improved Synthesis of 10β-Methyl-7α-isopropenyl-5β-hydroxy-3-decalone
Chen, Edward Y.
, p. 927 - 932 (2007/10/02)
An improved synthesis of the title compound using tetramethylammonium hydroxide as catalyst is described.
