21850-67-9

Basic information

• Product Name: TURNEFORCIDINE
• Synonyms: TURNEFORCIDINE;(1R)-2,3,5,6,7,7aα-Hexahydro-7β-hydroxy-1H-pyrrolizine-1-methanol;(1R,7aα)-7β-Hydroxyhexahydro-1H-pyrrolizine-1α-methanol;(1R,7R,8R)-Turneforcidine
• CAS NO: 21850-67-9
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.2102
• Mol File: 21850-67-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: TURNEFORCIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: TURNEFORCIDINE(21850-67-9)
• EPA Substance Registry System: TURNEFORCIDINE(21850-67-9)

Safety Data

• Hazardous Substances Data: 21850-67-9(Hazardous Substances Data)

Usage

Description

Turneforcidine is an alkaloid that has been found in small quantities in the extract from Turneforcia sibirica. It crystallizes as colorless needles from Me2CO and has a specific optical rotation of [α]D 10.5°. It is likely an artifact formed by the hydrolysis of Turneforcine during the extraction process.

Uses

There is no information provided in the materials about the specific uses of Turneforcidine. However, based on its classification as an alkaloid, it may have potential applications in various fields such as pharmaceuticals, agriculture, or chemical research. Further investigation and research would be required to determine its specific uses and potential benefits.

References

Men'shikov, Denisova, Massagetov., J. Gen. Chern., USSR, 22, 1465 (1952)

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Relevant articles and documents

Genus crotalaria. XVII. The stereochemistry of croalbinecine

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Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases

The endemic Mexican genus Pittocaulon (subtribe Tussilagininae, tribe Senecioneae, Asteraceae) belongs to a monophyletic group of genera distributed in Mexico and North America. The five Pittocaulon species represent shrubs with broom-like succulent branches. All species were found to contain pyrrolizidine alkaloids (PAs). With one exception (i.e., stems of Pittocaulon velatum are devoid of PAs) PAs were found in all plant organs with the highest levels (up to 0.3% of dry weight) in the flower heads. Three structural types of PAs were found: (1) macrocyclic otonecine esters, e.g. senkirkine and acetylpetasitenine; (2) macrocyclic retronecine esters, e.g. senecionine, only found in roots, and (3) monoesters of 1,2-saturated necines with angelic acid. For an unambiguous assignment of the different stereoisomeric 1,2-saturated necine bases a GC-MS method was established that allows the separation and identification of the four stereoisomers as their diacetyl or trimethylsilyl derivatives. All otonecine esters that generally do not form N-oxides and the 1,2-saturated PAs were exclusively found as free bases, while the 1,2-unsaturated 7-angeloylheliotridine occurring in P. velatum was found only as its N-oxide. In a comparative study the 1H and 13C NMR spectra of the four stereoisomeric necine bases were completely assigned by the use of DEPT-135, H,H-COSY, H,C-HSQC and H,H-NOESY experiments and by iterative analysis of the 1H NMR spectra. Based on these methods the PA monoesters occurring in Pittocaulon praecox and P. velatum were assigned as 7-O-angeloyl ester respectively 9-O-angeloyl ester of dihydroxyheliotridane which could be identified for the first time as naturally occurring necine base. Unexpectedly, in the monoesters isolated from the three other Pittocaulon species dihydroxyheliotridane is replaced by the necine base turneforcidine with opposite configuration at C-1 and C-7. The species-specific and organ-typical PA profiles of the five Pittocaulon species are discussed in a biogenetic context.

A facile synthesis of (-)- and (+)-Geissman-Waiss lactone via intramolecular Rh(II)-carbenoid mediated C-H insertion reaction: Synthesis of (1R,7R,8R)-turneforcidine

The intramolecular C-H insertion reaction in chiral non-racemic diazoacetates (-)-6 and (+)-8 catalyzed by chiral Rh2(MPPIM)4 proceeded efficiently, with excellent regioselectivity and cis-diastereoselectivity, to give (-)- and (+)-G