60419-55-8

Upstream product

• 16802-11-2 (+/-)-boschnialactone 
• 100475-84-1 -2 ethanoate de tert-butyle 
• 2436-90-0 (S)-(+)-dihydromyrcene 
• 131726-13-1 (4aR,7S,7aR)-Hexahydro-7-methylcyclopenta[c]pyran-3-one 
• 109-94-4 formic acid ethyl ester 
• 93904-58-6 (S)-4-methyl-5-hexenal 
• 24512-63-8 geniposide 
• 26660-57-1 deoxyloganin 
• 196509-95-2 deoxyloganin aglycone 
• 60419-57-0 2-[(1S,2R,3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]-2-propen-1-ol 
• 16802-11-2 (+/-)-(4aα,7α,7aα)-hexahydro-7-methylcyclopentapyran-3(1H)-one 
• 89502-74-9 (1R,3R,6R,7S,9R)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-one 
• 89502-66-9 (1R,4R,5S,6R)-5-Hydroxymethyl-6-methyl-bicyclo[2.2.1]heptan-2-one 
• 89502-68-1 (4aS,7S,7aR)-7-Methyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol 

Downstream Products

• 485-43-8 isoiridomyrmecin 
• 485-43-8 iridomyrmecin 

Relevant academic research and scientific papers

Application of Cp2TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes

An expedient approach toward the unified total syntheses of (+)-iridomyrmecin, (-)-isoiridomyrmecin, (+)-7-epi-boschnialactone, (+)-teucriumlactone, and (-)-dolichodial in chirally pure forms starting from readily available (+)-β-citronellene is delineated combining step economy and simplicity. Highlights include a Ti(III)-mediated reductive epoxide opening-cyclization for the construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones with complete diastereoselectivity for the newly created bridgehead stereogenic centers. Subsequent transformations facilitate a short access to (+)-teucriumlactone and (-)-dolichodial and formal access to potentially other iridoids.

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.

IRIDOIDS : STEREOSPECIFIC SYNTHESIS OF FUNCTIONALIZED CYCLOPENTANOID INTERMEDIATES VIA BICYCLOHEPTANONES

An efficient synthesis of functionalized trialkyl substituted cyclopentanoids is presented.Stereocontrol is secured by their formation from norbornane precursors.The strategy is illustrated by the total synthesis of (+/-)-boschnialactone (13), (+/-)-teucriumlactone C (14), and (+/-)-loganin (2).