466-49-9

Usage

Chemical Description

Aspidospermine is another alkaloid that is structurally similar to Quebrachamine and is used in the synthesis of methoxyquebrachamine.

Uses

Used in Pharmaceutical Industry:
ASPIDOSPERMINE is used as a respiratory stimulant for the treatment of respiratory conditions. Its ability to stimulate the respiratory system makes it a valuable compound in the development of medications aimed at improving breathing and overall respiratory health.
Used in Chemical Industry:
Due to its solubility in various solvents, ASPIDOSPERMINE can be used as an additive or intermediate in the chemical industry. Its unique chemical properties may allow for the creation of new compounds or the enhancement of existing ones, contributing to the development of novel products and materials.
Used in Research and Development:
ASPIDOSPERMINE's unique structure and properties make it an interesting compound for research and development purposes. Scientists and researchers can study its properties and interactions with other molecules to potentially discover new applications and uses for this alkaloid.

Safety Profile

A poison by intraperitoneal route.When heated to decomposition it emits toxic vapors ofNOx.

InChI:InChI=1/C22H30N2O2/c1-4-21-10-6-13-23-14-12-22(20(21)23)16-7-5-8-17(26-3)19(16)24(15(2)25)18(22)9-11-21/h5,7-8,18,20H,4,6,9-14H2,1-3H3/t18-,20-,21-,22-/m1/s1

Upstream product

• 1371593-14-4 C₂₃H₁₉NO₂ 
• 108-24-7 acetic anhydride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 2912-26-7 (+)-dehydrodeacetylaspidospermine 
• 2447-50-9 (+)-deacetylaspidospermine 
• 426-83-5 (9Ξ)-1-acetyl-17-methoxy-aspidospermidine-9-oxide 
• 67-56-1 methanol 
• 2111-81-1 1-(3a-ethyl-2,3,3a,4,5,5a,11,12-octahydro-1H-indolizino[8,1-cd]carbazol-6(3a¹H)-yl)ethan-1-one 

Downstream Products

• 88198-98-5 aspidospermine 
• 2447-50-9 (+)-deacetylaspidospermine 

Relevant academic research and scientific papers

Total Syntheses of Aspidospermidine, N-Methylaspidospermidine, N-Acetylaspidospermidine, and Aspidospermine via a Tandem Cyclization of Tryptamine-Ynamide

The total syntheses of aspidospermidine, N-methylaspidospermidine, N-acetylaspidospermidine, and aspidospermine were achieved from a common pentacyclic indoline intermediate. The common pentacyclic indoline intermediate was synthesized on a gram scale through a Stork-enamine alkylation of 1H-pyrrolo[2,3-d]carbazole derivatives, which were prepared through a Br?nsted acid-catalyzed tandem cyclization of tryptamine-ynamide. The scalable synthesis of 1H-pyrrolo[2,3-d]carbazole afforded facile access and a practical approach to the Aspidosperma indole alkaloid family.

Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products

A uniformly strategic total synthesis of Aspidosperma alkaloids (+)-vincadifformine, (-)-quebrachamine, (+)-aspidospermidine, (-)-aspidospermine, (-)-pyrifolidine, and nine others from efficiently constructed tricyclic ketone 13 is reported. Highlights of these divergent and practical syntheses include (i) stereoselective intermolecular [4 + 2] cycloaddition to establish a C-E ring with one all-carbon quaternary stereocenter (C-5) and two bridged contiguous cis-stereocenters (C-12 and C-19), (ii) a Pd/C-catalyzed hydrogenation/deprotection/amidation cascade process to assemble the D ring, and (iii) Fischer indolization to forge the A-B ring.

Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine

Divergent total syntheses of (+)-spegazzinine (1) and (-)-aspidospermine (2) and their extensions to the synthesis of C19-epi-aspidospermine and C3-epi-spegazzinine are detailed, confirming the relative stereochemistry and establishing the absolute configuration of (+)-spegazzinine. A powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole provided the pentacyclic skeleton and all the requisite stereochemistry of the natural products in a single reaction that forms three rings, four C-C bonds, and five stereocenters.

Highly efficient synthesis of tricyclic amines by a cyclization/ cycloaddition cascade: Total syntheses of aspidospermine, aspidospermidine, and quebrachamine

(Chemical Equation Presented) Three in one: Three new rings can be made in one pot with complete control of the regio- and stereochemistry by a tandem cyclization/cycloaddition cascade reaction. Treatment of a chloroaldehyde with an amine gives a cyclic azomethine ylide that undergoes intramolecular cycloaddition onto a tethered alkene. The method was applied to the shortest known synthesis of aspidospermine (see scheme).

Total synthesis of (-)-aspidospermine via diastereoselective ring-closing olefin metathesis

(Matrix presented) An enantiocontrolled total synthesis of (-)-aspidospermine has been achieved. The key element of the strategy is the diastereoselective construction of the quaternary stereogenic center employing 1,4-asymmetric induction during the ring-closing olefin metathesis.