15539-10-3

Basic information

• Product Name: (21R)-(+)-vincadifformine
• CAS NO: 15539-10-3
• Molecular Weight: 338.45
• Mol File: 15539-10-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 96 °C
• Boiling Point: 474.5±45.0 °C(Predicted)
• Density: 1.24±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (21R)-(+)-vincadifformine(CAS DataBase Reference)
• NIST Chemistry Reference: (21R)-(+)-vincadifformine(15539-10-3)
• EPA Substance Registry System: (21R)-(+)-vincadifformine(15539-10-3)

Safety Data

• Hazardous Substances Data: 15539-10-3(Hazardous Substances Data)

Upstream product

• 55475-53-1 20-iodo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester 
• 7013-58-3 (+)-aspidospermidine 
• 17640-15-2 methyl cyanoformate 
• 19751-76-9 (+)-1,2-didehydroaspidospermidine 
• 1263381-01-6 3-ethyl-5-bromo-2-pyrone 
• 4724-62-3 (3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one 
• 74129-83-2 (+)-(hydroxymethyl)norvincadifformine 
• 80658-39-5 C₂₁H₂₅ClN₂O₂ 

Downstream Products

• 18374-17-9 (±)-vincadifformine 
• 260362-01-4 14α-phenylselenenyl-3-oxo-(N_a-tert-butoxycarbonyl)-vincadifformine 
• 260362-12-7 14β-phenylselenenyl-3-oxo-(N_a-tert-butoxycarbonyl)-vincadifformine 
• 260362-00-3 14β-benzyl-3-oxo-(N_a-tert-butoxycarbonyl)vincadifformine 
• 260362-03-6 14β-benzyl-(N_a-tert-butoxy-carbonyl)vicadifformine 
• 260362-08-1 14β-benzyl-1,2-didehydroaspidospermidine 
• 19751-76-9 (+)-1,2-didehydroaspidospermidine 

Relevant articles and documents

16-EPI-19-S-VINDOLININE, AN INDOLINE ALKALOID FROM CATHARANTHUS ROSEUS

Key Word Index - Catharanthus roseus; Apocynaceae; leves; indole alkaloids; 13C NMR; 16-epi-19-S-vindolinine. Studies on the aslkaloids of Catharanthus roseus have resulted in the isolation of a new alkaloid, to which the structure of 16-epi-19-S-vindolinine has been assigned.

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Asymmetric Total Synthesis of Vincadifformine Enabled by a Thiourea-Phosphonium Salt Catalyzed Mannich-Type Reaction

An asymmetric total synthesis of vincadifformine is described. The limited tactics with chiral cation-directed catalysis in total synthesis inspired the development of our strategy for accessing this alkaloid in enantionrich form. The route features a thiourea–phosphonium salt catalyzed Mannich-type reaction, a phosphine-promoted aza-Morita–Baylis–Hillman reaction and a trifluoroacetic acid promoted deprotection/amidation cascade process.

Collective synthesis of natural products by means of organocascade catalysis

Organic chemists are now able to synthesize small quantities of almost any known natural product, given sufficient time, resources and effort. However, translation of the academic successes in total synthesis to the large-scale construction of complex natural products and the development of large collections of biologically relevant molecules present significant challenges to synthetic chemists. Here we show that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold. The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine.