108377-11-3

Upstream product

• 89502-66-9 (1R,4R,5S,6R)-5-Hydroxymethyl-6-methyl-bicyclo[2.2.1]heptan-2-one 
• 28839-89-6 (1S,2S,3S,6S,7R,9S)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol 
• 89502-74-9 (1R,3R,6R,7S,9R)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-one 
• 542-92-7 cyclopenta-1,3-diene 
• 108449-68-9 (5R, 6S)-5-endo-hydroxymethyl-6-exo-methylbicyclo<2.2.1>-2-heptanone 
• 108448-78-8 (1R, 2R, 4R, 5R)-4-exo-methyl-tricyclo<(3.2.1.1)^3,8>-7-oxa-2-exo-nonanol 
• 108448-79-9 (1R, 4R, 5R)-4-exo-methyl-tricyclo<(3.2.1.1.)^3,8>-7-oxa-2-nonanone 
• 94668-49-2 (1R,2R,3S,4S)-3-methyl-5-norbornene-2-methanol 

Downstream Products

• 108448-80-2 7-O-benzoyl-1-α-O-methyl-loganin aglucone 
• 108377-16-8 7-O-benzoyl-1-O-methyl-loganin aglucone 
• 108377-15-7 (1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester 
• 68736-83-4 (1R)-1-O-methyl loganin aglycone 
• 23661-17-8 (4aS,6R,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

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.

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).