68736-83-4

Upstream product

• 108377-16-8 7-O-benzoyl-1-O-methyl-loganin aglucone 
• 108448-78-8 (1R, 2R, 4R, 5R)-4-exo-methyl-tricyclo<(3.2.1.1)^3,8>-7-oxa-2-exo-nonanol 
• 124-41-4 sodium methylate 
• 29748-09-2 7-O-acetyl-8-epiloganol 
• 28839-89-6 (1S,2S,3S,6S,7R,9S)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol 
• 89502-70-5 (1R,4R,5S,6R)-5-[1,3]Dioxolan-2-yl-6-methyl-bicyclo[2.2.1]heptan-2-one 
• 108377-11-3 (1R,2S,3R,4R)-3-Methyl-5-oxo-bicyclo[2.2.1]heptane-2-carbaldehyde 
• 67-56-1 methanol 
• 94668-49-2 (1R,2R,3S,4S)-3-methyl-5-norbornene-2-methanol 
• 108377-15-7 (1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester 
• 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 

Relevant academic research and scientific papers

Modified iridoid glycosides as anti-implantation agents: Inhibition of cell adhesion as an approach for developing pregnancy interceptive agents

Structural modifications in iridoid glycosides and evaluation of their efficacy on adhering capability (in vitro) of immature hamster uterine epithelial cells to the substratum have been studied. Out of 31, eight compounds in vitro, five compounds in utero and two in vivo showed adhesion/implantation preventing activity, respectively. The results provide an indication for further exploration in the line of development of anti-adhesive agents.

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.

THE BITTER IRIDOIDS FROM VIBURNUM URCEOLATUM

Four new bitter iridoid glucosides, including three bis-iridoids, were isolated from Viburnum urceolatum and their structures elucidated.They are composed of loganin or deoxyloganin as the aglucone esterified with either aromatic glucoside or with glucose in the 4-position.Key Word Index-Viburnum urceolatum; Caprifoliaceae; iridoids; urceloatoside A-D; bitter components.

IRIDOIDS: THE TOTAL SYNTHESIS OF THE AGLUCONES OF (+/-)-8-EPILOGANIN AND (+/-)-MUSSAENOSIDE VIA BICYCLOOCTENES

The nitrone-olefin cycloaddition reaction has been used to construct cisfused bicyclooctanes or diquinanes as potential intermediates for C-11 functionalized iridoids.The isoxaolidine 7 was obtained in four steps from the commercially available 2-cyclopentene-1-acetic acid 4.Different functionalized diquinanes 8 to 19 and 22 to 24 have been prepared.As illustrative examples of iridoid synthesis, compounds 21 and 26, the O-methyl protected aglucones of (+/-)-8-epiloganin (2) and (+/-)-mussaenoside (3) have been synthesized starting from the common key-intermediate 11.

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).