80734-66-3

Upstream product

• 63573-60-4 8-epi-11-hydroxy-iridodial glucoside 
• 24512-66-1 8-epi-deoxyloganin tetraacetate 
• 26660-57-1 8-epi-deoxyloganin 
• 75252-39-0 8(S)-6,10-dideoxy-7,8-dihydroaucubin tetraacetate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 27934-98-1 ipolamiide 
• 27856-54-8 lamiide 
• 72963-60-1 Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1S,7S)-4-formyl-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-1-yloxy)-tetrahydro-pyran-3-yl ester 
• 17948-85-5 3(R)-trans,trans-boschnialinic acid 
• 75252-39-0 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1S,4aR,7R,7aR)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-1-yloxy)-tetrahydro-pyran-3-yl ester 
• 75252-40-3 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-((1S,4aR,7R,7aR)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-1-yloxy)-tetrahydro-pyran-3,4,5-triol 
• 75252-41-4 (4aR,7R,7aR)-7-Methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-1-ol 
• 20314-41-4 3(R)-cis,cis-boschnialinic acid 
• 75282-53-0 7-deoxy-8-epi-loganic acid tetraacetate 
• 72963-60-1 boschnaloside tetraacetate 

Relevant academic research and scientific papers

BIOSYNTHESIS OF ANTIRRHINOSIDE IN ANTIRRHINUM MAJUS

Feeding experiments with deuterium labelled 8-epi-iridodial glucoside, 8-epi-iridotrial glucoside and the corresponding aglucones gave incorporation of all compounds into antirrhinoside in Antirrhinum majus.A higher incorporation of 8-epi-iridotrial than of 8-epi-iridotrial glucoside indicates that the former is an intermediate in the biosynthesis of antirrhinoside although a definite proof could not be obtained. Key Word Index - Antirrhinum majus; Scophulariaceae; antirrhinoside; 8-epi-deoxyloganic acid; 8-epi-iridodial; 8-epi-iridodial glucoside; 8-epi-iridotrial; 8-epi-iridotrial glucoside; iridoid glucosides; biosynthesis; 2H-labelling.

APPLICATION OF THE VILSMEIER FORMYLATION IN THE SYNTHESIS OF 11-(13)C LABELLED IRIDOIDS

The Vilsmeier reaction was utilized for the introduction of C-11 into iridoid glucosides, Aucubin hexaacetate (3a). 6,10-dideoxy aucubin tetraacetate (6a) and 8(S)-6,10-dideoxy-7,8-dihydro aucubin tetraacetate (7a) were used as substrates for the reaction. 6a and 7a were prepared by catalytic transfer hydrogenation of 3a with formic acid and Pd/C.The Vilsmeier reaction conditions were optimized with regard to the economic use of --DMF in the synthesis of -iridotrialglucoside (9).Remarcably, 5percent of the label in the product turned out to be situated at C-3.