27766-71-8

Basic information

• Product Name: pumiliotoxin C
• Synonyms: pumiliotoxin C
• CAS NO: 27766-71-8
• Molecular Formula: C13H25N
• Molecular Weight: 195.3443
• Mol File: 27766-71-8.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 261.4°Cat760mmHg
• Flash Point: 110.8°C
• Appearance: /
• Density: 0.854g/cm³
• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: 1.451
• CAS DataBase Reference: pumiliotoxin C(CAS DataBase Reference)
• NIST Chemistry Reference: pumiliotoxin C(27766-71-8)
• EPA Substance Registry System: pumiliotoxin C(27766-71-8)

Safety Data

• Hazardous Substances Data: 27766-71-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H25N/c1-3-5-11-8-9-12-10(2)6-4-7-13(12)14-11/h10-14H,3-9H2,1-2H3/t10-,11+,12+,13-/m1/s1

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Relevant articles and documents

Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products

Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

The asymmetric synthesis of (-)-pumiliotoxin C using tandem catalysis

The potent neurotoxin (-)-pumiliotoxin C has been prepared in 8 steps starting from 2-cyclohexenone. Key steps are a tandem asymmetric conjugate addition-allylic substitution reaction and a tandem Heck-allylic substitution reaction. Graphical Abstract.

Efficient asymmetric synthesis of pumiliotoxin C via intramolecular [4 + 2] cycloaddition

An efficient asymmetric synthesis in nine steps of natural (-)-pumiliotoxin C (1), a decahydroquinoline alkaloid found in the skin of Central American frog species, is presented. The enantiomerically pure starting material (S)-norvalinol (3) obtained from