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

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

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

• 132317-05-6 (1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine 
• 51704-42-8 deacetylslaframine 
• 142723-00-0 slaframine azide 
• 153379-66-9 (1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate 
• 164324-15-6 (1S,8aS)-6-(Hydroxyimino)-1,2,3,5,6,7,8,8a-octahydroindolizinyl acetate 
• 457614-07-2 (2S,5S,6S)-5-azido-6-benzyloxy-2-[(tert-butoxycarbonyl)amino]-1,8-[(methylsulfonyl)oxy]octane 
• 118449-01-7 (2R,3S)-3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 131347-78-9 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 131270-20-7 ethyl (2R,3S)-N-benzoxycarbonyl-3-hydroxypyrrolidine-2-carboxylate 
• 131270-21-8 (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 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 
• 126645-93-0 4-<(tert-butyldimethylsilyl)oxy>-3,4-dihydro-5-methyl-2H-pyrrole 
• 1026808-68-3 [(1S,6R)-1-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-1,2,3,5,6,7-hexahydro-indolizin-6-yl]-carbamic acid tert-butyl ester 

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

Highly Enantioselective Approach to Indolizidines: Preparation of (+)-(1S,8aS)-1-Hydroxyindolizidine and (-)-Slaframine

A highly stereoselective approach to (-)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloaddition of dichloroketene with a chiral dienol ether.

Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Synthesis of (-)-Slaframine

(matrix presented) (-)-slaframine An asymmetric synthesis of (-)-slaframine and N-acetylslaframine has been accomplished starting from an enantiopure dihydropyridone building block. The oxygen-carbon bond at C-1 was incorporated with complete stereoselect

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.

A total synthesis of (-)-slaframine from (+)-cis-(2R,3S)-3-hydroxyproline

A total synthesis of the naturally occurring indolizidine (-)-Slaframine 4 has been achieved, starting from the cis-3-hydroxyproline derivative 1, in which a key step is a Julia olefination reaction using the dianion derived from the β-aminosulfone 5.

Synthesis of (-)-Slaframine and Related Indolizidines

An enantioselective synthesis of the indolizidine alkaloid (-)-slaframine 1 is reported.Reductive double cyclization of the azido epoxy tosylate 48 afforded the indolizidine 52, which was converted to (-)-slaframine in two steps.The cyclization substrate

A Novel Thermolytic Annulation of an Oxazolidinone: An Enantiospecific Synthesis of (-)-Slaframine

Optically pure β-aminopiperidines can be prepared in high yields through a thermolytic annulation sequence involving ring opening of an oxazolidinone.