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Usage

Uses

Used in Pharmaceutical Industry:
(16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester is used as a potential therapeutic agent for various medical conditions due to its anti-inflammatory, analgesic, and anti-cancer properties. Its potential in treating neurological disorders, such as Alzheimer's disease, also makes it a valuable compound for further research and development in the pharmaceutical industry.
Used in Biotechnology Industry:
(16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester is used as a promising candidate for the development of novel pharmaceuticals and drug delivery systems in the biotechnology industry. Its improved stability and bioavailability as a methyl ester form make it suitable for various applications in medicine and biotechnology, including the creation of innovative drug formulations and targeted therapies.

Relevant academic research and scientific papers

Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies

The akuammiline alkaloids are a structurally diverse class of bioactive natural products isolated from plants found in various parts of the world. A particularly challenging subset of akuammiline alkaloids are those that contain a methanoquinolizidine core. We describe a synthetic approach to these compounds that has enabled the first total syntheses of (+)-strictamine, (-)-2(S)-cathafoline, (+)-akuammiline, and (-)-ψ-akuammigine. Our strategy relies on the development of the reductive interrupted Fischer indolization reaction to construct a common pentacyclic intermediate bearing five contiguous stereocenters, in addition to late-stage formation of the methanoquinolizidine framework using a deprotection-cyclization cascade. The total syntheses of (-)-ψ-akuammigine and (+)-akuammiline mark the first preparations of akuammiline alkaloids containing both a methanoquinolizidine core and vicinal quaternary centers. Lastly, we describe the bioinspired reductive rearrangements of (+)-strictamine and (+)-akuammiline to ultimately provide (-)-10-demethoxyvincorine and a new analogue thereof.

Total Syntheses of Echitamine, Akuammiline, Rhazicine, and Pseudoakuammigine

Echitamine (1) and akuammiline (2) are representative members of a fascinating class of monoterpenoid indole alkaloids. We report the syntheses of 2 and its congener deacetylakuammiline (3). The azabicyclo[3.3.1]nonane motif was assembled through silver-catalyzed internal alkyne cyclization, and one-pot C?O bond cleavage/C?N bond formation furnished the pentacyclic scaffold. Compound 3 then served as a common intermediate for preparing a series of structurally diverse and synthetically challenging congeners including 1. A position-selective Polonovski–Potier reaction followed by formal N-4 migration built the core of N-demethylechitamine (4) and 1. An alternative route featuring Meisenheimer rearrangement gave 4 as well. Oxidation of the alcohol within 3 gave rhazimal (5), which underwent tandem indolenine hydrolysis, hemiaminalization, and hemiketalization to form rhazicine (6). A sequence of N,O-ketalization and reductive amination secured the chemoselectivity of N-methylation, leading to pseudoakuammigine (7).

ALSTOLENINE, 19,20-DIHYDROPOLYNEURIDINE AND OTHER MINOR ALKALOIDS OF THE LEAVES OF ALSTONIA VENENATA

Structures of alstolenine and 19,20-dihydropolyneuridine, two new indole alkaloids of the leaves of Alstonia venenata have been established.In addition, deacetylakuammiline, polyneuridine and raucaffrinoline have been isolated for the first time from this plant.Key Word Index-Alstonia venenata; Apocynaceae; alstolenine; 19,20-dihydropolyneuridine; polyneuridine; deacetylakuammiline; raucaffrinoline; indol alkaloids.