20084-93-9

Basic information

• Product Name: slaframine
• Synonyms: slaframine;(1S,8aα)-6β-Aminooctahydroindolizin-1β-ol acetate
• CAS NO: 20084-93-9
• Molecular Formula: C₁₀H₁₈N₂O₂
• Molecular Weight: 198.264
• Mol File: 20084-93-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 278.5°Cat760mmHg
• Flash Point: 122.2°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.00425mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: slaframine(CAS DataBase Reference)
• NIST Chemistry Reference: slaframine(20084-93-9)
• EPA Substance Registry System: slaframine(20084-93-9)

Safety Data

• Hazardous Substances Data: 20084-93-9(Hazardous Substances Data)

Usage

Description

Slaframine is an indolizidine alkaloidal mycotoxin that is produced by the fungus Rhizoctonia leguminicola and is known to cause excessive salivation in most animals. It is an amorphous base that yields an amorphous dihydrochloride and crystalline dipicrate and N-acetyl derivatives. The structure of slaframine has been revised to 1-acetoxy-6-aminooctahydroindolizidine with a configuration of 1S,6S,8aS-.

Uses

Slaframine is used as a veterinary agent for the treatment of excessive salivation in animals caused by legume forages infested by Rhizoctonia leguminicola. It is also used as a research tool in the study of the effects of mycotoxins on animal health and behavior.

References

Rainey et al., Nature, 205, 203 (1965) Aust, Broquist., ibid, 205, 204 (1965) Aust, Broquist, Rinehart.,l. Arner. Chern. Soc., 88,2879 (1966) Whitlock et al., Tetrahedron Lett., 3819 (1966) Revised structure: Gardiner et al., J. Arner. Chern. Soc., 90,5639 (1968)

InChI:InChI=1/C10H18N2O2/c1-7(13)14-10-4-5-12-6-8(11)2-3-9(10)12/h8-10H,2-6,11H2,1H3/t8-,9-,10-/m0/s1

Upstream product

• 146987-16-8 (1S,6R,8aS)-1-acetoxy-6-<(tert-butoxycarbonyl)amino>-1,2,3,5,6,7,8,8a-octahydroindolizine 
• 153277-21-5 (R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane 
• 153379-66-9 (1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate 
• 130966-41-5 Methyl (2R,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylate 
• 153277-24-8 (2S,3S)-1-(tert-Butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-methanol 
• 153277-25-9 (2R,3S)-1-(tert-Butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-carbaldehyde 
• 153379-64-7 O-Deacetyl-N-(benzyloxycarbonyl)slaframine 
• 194924-97-5 Methyl (2R,3S)-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine-2-carboxylate 
• 153277-29-3 ((1S,6S,8aS)-1-Methoxymethoxy-octahydro-indolizin-6-yl)-carbamic acid benzyl ester 
• 153277-31-7 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-hydroxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-32-8 (2S,3S)-2-((S)-3-Benzyloxycarbonylamino-4-methanesulfonyloxy-butyl)-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 153277-28-2 (2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine 
• 153277-26-0 (2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine 
• 126645-93-0 4-<(tert-butyldimethylsilyl)oxy>-3,4-dihydro-5-methyl-2H-pyrrole 

Downstream Products

• 153379-66-9 (1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate 

Relevant articles and documents

Enantioselective allyltitanation. Synthesis of (-)-slaframine

An enantioselective synthesis of the indolizidine alkaloid (-)-slaframine from aldehyde 1 is reported. The stereogenic centers at C-1 and C-8a are introduced by an enantioselective allyltitanation and a Mitsunobu reaction. Reductive double cyclization of

Enantiospecific Synthesis of (-)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine 1

A general methodology for the synthesis of indolizidine alkaloids δ-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.

Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline

The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergoes an efficient Julia olefination with the L-serine-derived amino sulfone 29. Selective reduction of the resulting alkene 31 using diimide and cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural (-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.