Ozonolytic Decyclization of (R)-4-Menthen-3-one

Ozonolytic decyclization of (R)-4-menthen-3-one is accompanied by fragmentation of the isobutyl group, leading to -functionalized 3-methylpentanoic acid derivatives.     

Synthesis of the Juvenoid (S)-(+)-Hydroprene from L-(-)-Menthol

The versatile chiral synthon methyl (R)-5,5-dimethoxy-3-methylpentanoate has been prepared for the first time via ozonolytic decyclization of (R)-4-menthenone, which is available from L-(-)-menthol. The optically pure juvenoid (S)-(+)-hydroprene can be prepared from the synthon     

Insect Pheromones Synthesized by Oxidative Transformations of Natural Monoterpenoids

The literature on oxidative transformations of natural monoterpenoids to synthesize insect pheromones was reviewed. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 509–522, November–December, 2005.     

Synthesis of (3S,6RS)- and (3RS,6RS)-Analogs of Component AI of the Aonidiella aurantii Sex Pheromone by Stepwise Alkylation of Acetoacetic Ester

Synthetic approaches to (±)- and (3S)-analogs of the AI component of the Aonidiella aurantii sex pheromone (3S)-methyl-6R-isopropenyldec-9-en-1-ylacetate based on stepwise alkylation of acetoacetic ester by 3-butenylbromide and 1,5-bifunctional 3-methylpentanes were investigated. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 589–591, November–December, 2005.     

Synthesis of 3S-methylundec-1-ylbromide, a key synthon in the synthesis of (S,S,S)-diprionylacetate, from L-(-)-menthol

Three new approaches to the synthesis of 1-bromo-3S-methylundecane, a key synthon in the synthesis of (S,S,S)-diprionylacetate, a sex pheromone of pine sawflies of the genera Diprion and Neodiprion, were proposed based on chemo-and stereoselective transformations of L-(-)-menthol derivatives. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 73–76, January–February, 2006.     

A useful chiral synthon from (R)-4-menthenone

Russian Chemical Bulletin -