75281-29-7

Upstream product

• 24512-63-8 geniposide 
• 75222-58-1 (1R)-1-methoxymyodesertan 
• 19479-28-8 (-)-(1R)-1-methoxymyodesert-3-ene 
• 26660-57-1 deoxyloganin 
• 142603-55-2 Acetic acid (1R,4aS,7S,7aR)-1-(2-ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-ylmethyl ester 
• 142603-53-0 (1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 142603-54-1 [(1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-yl]-methanol 
• 196509-95-2 deoxyloganin aglycone 
• 142603-56-3 (1R,4aS,7S,7aR)-1-(2-Ethoxy-ethoxy)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran 
• 142603-57-4 (1S,4R,4aR,7S,7aR)-1-(2-Ethoxy-ethoxy)-4,7-dimethyl-octahydro-cyclopenta[c]pyran 

Downstream Products

• 35337-15-6 (4R,4aR,7R,7aR)-4,7-Dimethyl-hexahydro-cyclopenta[c]pyran-1-one 
• 490-09-5 (4R,4aR,7R,7aS)-4,7-Dimethyl-hexahydro-cyclopenta[c]pyran-1-one 

Relevant academic research and scientific papers

SYNTHESIS OF IRIDOLACTONES ISOLATED FROM SILVER VINE

The naturally occurring iridolactones, nepetalactone, isodihydronepetalactone, and iridomyrmecin are synthesized in optically active forms starting from natural glycoside geniposide.The stereogenic centers were introduced with highly stereoselective hydrogenations.

Terpenoid Chemistry. XXIV (1R)-1-Methoxymyodesert-3-ene, an Iridoid Constituent of Myoporum deserti (Myoporaceae)

A common variety of Myoporum deserti A.Cunn. (Ellangowan Poison Bush) yields an essential oil consisting largely of the iridoid monoterpene, (1R)-1-methoxymyodesert-3-ene, C11H18O2, (1R,4aS,7R,7aR)-1-methoxy-4,7-dimethyl-1,4a,5,6,7,7a-hexahydrocyclopentapyran, b.p. 67 deg/2 mm, D - 165 deg.This cyclic acetal is hydrolysed to methanol and a mixture of two epimeric cyclopentanoid dialdehydes which are oxidized to the two epimeric trans, trans-nepetalinic acids and yield (+)-(R)-actinidine with Brady's reagent, (1R)-1-Methoxymyodesert-3-ene is oxidized by ozone/hydrogen peroxide to (1R,2R,5R)-2-acetyl-5-methylcyclopentanecarboxylic acid.Hydrogenation yields mainly (1R)-methoxymyodesertan, hydrolysed by aqueous maleic acid at room temperature to methanol and a cyclic hemiacetal, (1R,4R,4aR,7R,7aR)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol.Oxidation of this cis,cis-hemiacetal by bromine in acetate buffer yields a lactone further oxidized by chromic acid to (2R,1',S',2'R,3'R)-2-(2'-carboxy-3'-methylcyclopentyl)-propionic acid. (1R)-1-Methoxymyodesertan, refluxed with aqueous phthalic acid, yields (+)-(4R,4aR,7R)-4,7-dimethyl-3,4,4a,5,6,7-hexahydrocyclopentapyran.Treatment of the hexahydropentapyran, the cis,cis-hemiacetal or (1R)-1-methoxymyodesertan with hydrochloric acid yields a trans,trans-hemiacetal, (1R,4R,4aR,7R,7aS)-4,7-dimethyl-1,3,4,4a,5,6,7,7a-octahydrocyclopentapyran-1-ol,which equilibrates in solution to a mixture of α- and β-anomers.Spectral studies of these and other products establish the configuration of the natural product at C1. (1R)-1-Methoxymyodesert-3-ene is not toxic to sheep as are the β-substituted furans characteristic of most other chemovarieties of M. deserti.