18397-07-4

Basic information

• Product Name: pereirine
• Synonyms: Geissoschizoline; Pereirine; (15beta,16alpha,20alpha)-curan-17-ol
• CAS NO: 18397-07-4
• Molecular Formula: C₁₉H₂₆N₂O
• Molecular Weight: 298.4225
• EINECS: 242-275-1
• Mol File: 18397-07-4.mol

Chemical Properties

• Boiling Point: 467.8°C at 760 mmHg
• Flash Point: 236.7°C
• Density: 1.23g/cm³
• Vapor Pressure: 1.49E-09mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: pereirine(CAS DataBase Reference)
• NIST Chemistry Reference: pereirine(18397-07-4)
• EPA Substance Registry System: pereirine(18397-07-4)

Safety Data

• Hazardous Substances Data: 18397-07-4(Hazardous Substances Data)

Upstream product

• 2912-08-5 (-)-19,20-dihydroakuammicine 
• 639-43-0 (-)-akuammicine 
• 1322613-98-8 C₁₆H₁₈N₂O₂ 
• 7267-97-2 curan-17-oic acid methyl ester 

Downstream Products

• 1233498-33-3 (-)-leucoridine C 

Relevant articles and documents

Biomimetic assembly of leucoridine A

The three-step biomimetic assembly of leucoridine A, a pseudosymmetric bisindole of Leuconotis griffithi (Apocynaceae) is described. The semisynthetic route provides suitable conditions toward the central 3-spiro-1,2,3,4-tetrahydropiperidine ring connecting the two subunits of the highly congested structure. The biomimetic assembly by a Diels-Alder or alternatively an imino-Rauhut-Currier reaction affords the natural (S)-diastereomer of leucoridine A as the sole product. The sequence, repeated in a one-pot cascade, supports a non-enzymatic pathway for the assembly of this bisindole and the known related alkaloids. The biomimetic cascade assembly of leucoridine A, a pseudosymmetric bisindole of Leuconotis griffithi (Apocynaceae) is described. The semisynthetic route provides suitable conditions toward the central 3-spiro-1,2,3,4-tetrahydropiperidine ring connecting the two subunits of the highly congested structure. The biomimetic assembly by an imino-Rauhut-Currier reaction affords the natural (S)-diastereomer of leucoridine A as the sole product.

Biomimetic total syntheses of (-)-leucoridines A and C through the dimerization of (-)-dihydrovalparicine

Concise biomimetic syntheses of the Strychnos-Strychnos-type bis-indole alkaloids (-)-leucoridine A (1) and C (2) were accomplished through the biomimetic dimerization of (-)-dihydrovalparicine (3). En route to 3, the known alkaloids (+)-geissoschizoline (8) and (-)-dehydrogeissoschizoline (10) were also prepared. DFT calculations were employed to elucidate the mechanism, which favors a stepwise aza-Michael/spirocyclization sequence over the alternate hetero-Diels-Alder cycloaddition reaction. Concise biomimetic syntheses of the Strychnos-Strychnos-type bis-indole alkaloids (-)-leucoridine A and C were accomplished through the biomimetic dimerization of (-)-dihydrovalparicine. DFT calculations were used to elucidate the mechanism, which favors a stepwise aza-Michael/spirocyclization sequence over the alternate hetero-Diels-Alder cycloaddition reaction.