10285-06-0

Usage

Uses

Used in Pharmaceutical Industry:
INTERMEDINE is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs and treatments.
Used in Chemical Research:
INTERMEDINE is used as a research compound in the field of chemistry. Its unique structure and properties make it an interesting subject for study, potentially leading to new insights and discoveries in the field.
Used in Industrial Applications:
INTERMEDINE is used as an industrial chemical for its specific properties and reactivity. Its unique structure allows it to be used in various processes and applications, contributing to the development of new products and technologies.

InChI:InChI=1/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12-,13-,15+/m1/s1

Upstream product

• 72213-98-0 parsonsine 
• 20267-93-0 lycopsamine A N-oxide 
• 95462-10-5 (4S,5R)-4-Isopropyl-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 
• 95462-08-1 4(S)-(1-methylethyl)-2,2,5(R)-trimethyl-1,3-dioxolane-4-carboxylic acid 
• 480-85-3 retronecine 
• 23944-48-1 (2S,3R)-2,3-dihydroxy-2-(1-methylethyl)butyric acid 
• 23944-47-0 (+/-)-trachelanthic acid 
• 109305-71-7 1,2-O-isopropylidene-5-deoxy-3-C-isopropyl-β-D-lyxofuranose 
• 109305-72-8 1,2-O-isopropylidene-3-O-benzyl-5-deoxy-3-C-isopropyl-β-D-lyxofuranose 
• 109305-75-1 tetraol 
• 94773-28-1 trans-α-isopropylcrotonic acid 
• 109305-76-2 2-O-benzyl-(+)-trachelanthic acid 

Downstream Products

• 95462-14-9 intermedine N-oxide 

Related news

Preparative separation of the pyrrolizidine alkaloids, INTERMEDINE (cas 10285-06-0) and lycopsamine, as their borate complexes07/27/2019

Intermedine and lycopsamine are diastereoisomers containing vicinal glycol groups of different configuration. The difference in the degree to which they complex with borate is the basis of two procedures for their separation from mixtures on a preparative scale. In the first, the mixture dissolv...detailed

The total syntheses of (−)-indicine N-oxide and INTERMEDINE (cas 10285-06-0) N-oxide07/26/2019

The total syntheses of (−)-indicine N-oxide, the enantiomer of natural indicine N-oxide and intermedine N-oxide have been achieved.detailed

Relevant academic research and scientific papers

Enantiospecific synthesis of (+)- and (-)-trachelanthic acids via asymmetric dihydroxylation and their conversion to the pyrrolizidine alkaloids indicine and intermedine

Asymmetric dihydroxylation of (E)-ethyl 2-isopropylbut-2-enoate with AD-mix-a and AD-mix-P, followed by saponification, gives (-)- and (+)-trachelanthic acids, respectively, which are each coupled via their acetonides with (+)-retronecine to yield the pyrrolizidine alkaloids indicine and intermedine.

Ideamine N-Oxides: Pyrrolizidine Alkaloids Sequestered by the Danaine Butterfly, Idea leuconoe

Two new pyrrolizidine alkaloids, ideamines A and B, together with other analogs (lycopsamine and parsonsine) were isolated in the N-oxide forms from adult bodies of the Apocynaceae-feeding danaine butterfly, Idea leuconoe.Ideamine A was characterized as a homolog of lycopsamine, in which the viridifloric acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety.Likewise, ideamine B was identified as a nor-derivative of parsonsine, in which the trachelanthic acid moiety was replaced by a 2-ethyl-2,3-dihydroxybutanoic moiety diastereomeric to the necic acid from ideamine A.

THE TOTAL SYNTHESES OF (-)-INDICINE N-OXIDE AND INTERMEDINE N-OXIDE

The total syntheses of (-)-indicine N-oxide, the enantiomer of natural indicine N-oxide and intermedine N-oxide have been achieved.

Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents

(-)- and (+)-trachelanthic and (-)- and (+)-viridifloric acids were synthesized and their isopropylidene derivatives were regiospecifically coupled, at C-9, with (-)-retronecine (2) obtained by hydrolysis of monocrotaline (1), isolated from Crotalaria spectabilis. Hydrolysis, followed by oxidation, led to the N-oxides of indicine (7), intermedine (13), lycopsamine (15), and the new nonnatural product 16, respectively. Each of these analogues was screened in the P388 lymphocytic leukemia system at the same time as indicine N-oxide, and the results were compared. Other related analogues were prepared and similarly screened and the results compared with those from indicine N-oxide.