108448-80-2

Upstream product

• 108448-78-8 (1R, 2R, 4R, 5R)-4-exo-methyl-tricyclo<(3.2.1.1)^3,8>-7-oxa-2-exo-nonanol 
• 108449-68-9 (5R, 6S)-5-endo-hydroxymethyl-6-exo-methylbicyclo<2.2.1>-2-heptanone 
• 108377-11-3 (5R, 6S)-5-endo-formyl-6-exo-methylbicyclo<2.2.1>-2-heptanone 
• 94668-49-2 (1R,2R,3S,4S)-3-methyl-5-norbornene-2-methanol 
• 108377-14-6 (1R, 2S, 3R, 4R)-2-(dimethoxymethyl)-4-hydroxyl-3-methyl-1-cyclopentane acetic acid methyl ester 
• 108377-13-5 (5R, 6S)-6-endo-dimethoxymethyl-7-exomethyl-2-oxabicyclo<3.2.1>-3-octanone 
• 108377-12-4 (5R, 6S)-5-endo-dimethoxymethyl-6-exo-methylbicyclo<2.2.1>-2-heptanone 
• 108448-79-9 (1R, 4R, 5R)-4-exo-methyl-tricyclo<(3.2.1.1.)^3,8>-7-oxa-2-nonanone 
• 114217-64-0 [(2S,3S,4R,5S)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-4-yl]-acetaldehyde 
• 114217-63-9 (2S,3S,4S,5S)-4-Allyl-5-benzyloxy-2-methoxy-tetrahydro-pyran-3-ol 
• 108377-15-7 (1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester 
• 110-71-4 1,2-dimethoxyethane 
• 114244-09-6 Benzoic acid (1S,4aS,6S,7R,7aR)-1-methoxy-7-methyl-4-oxo-octahydro-cyclopenta[c]pyran-6-yl ester 

Relevant academic research and scientific papers

Cyclopentane-annelated Pyranosides: A New Approach to Chiral Iridoid Synthesis

1-α-O-Methyl-loganin (1) was synthesised from methyl 2,3-anhydro-α-D-lyxopyranoside by cyclopentane annulation using the pyranose ring as the tetrahydrocoumalate skeleton.

IRIDOIDS : ENANTIOSELECTIVE SYNTHESIS OF LOGANIN VIA AN ASYMMETRIC DIELS-ALDER REACTION

Starting from (-)-camphor-10-sulfonic acid (5) the crystalline sultam 9 was readily prepared.TiCl4-mediated Diels-Alder addition of the N-crotonyl sultam 11 to cyclopentadiene, crystallization of the resulrting adduct 12 and subsequent reduction gave virtually pure (1S, 4R,5R, 6S)-1 together with recovered auxiliary 9.The loganin precursor 1 was transformed into norbonanone 20, which upon Baeyer-Villiger oxidation led to the suitably substituted cyclopentane 22 from which 1-B-O-methyl loganin aglucone (2) was readily available.