Aspidospermidine, (+)-

Base Information

• Chemical Name: Aspidospermidine, (+)-
• CAS No.: 2912-09-6
• Molecular Formula: C₁₉H₂₆N₂
• Molecular Weight: 282.429
• UNII: 38EV97NHY2
• DSSTox Substance ID: DTXSID301045567
• Nikkaji Number: J39.325H
• Wikipedia: Aspidospermidine
• Wikidata: Q104402848
• Metabolomics Workbench ID: 52225
• Mol file: 2912-09-6.mol

Synonyms:aspidospermidine

Chemical Property of Aspidospermidine, (+)-

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 282.209598838
• Heavy Atom Count: 21
• Complexity: 435

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC12CCCN3C1C4(CC3)C(CC2)NC5=CC=CC=C45
• Isomeric SMILES: CC[C@]12CCCN3[C@H]1[C@@]4(CC3)[C@@H](CC2)NC5=CC=CC=C45

Technology Process of Aspidospermidine, (+)-

There total 122 articles about Aspidospermidine, (+)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

C26H26N2 → (+)-aspidospermidine (7013-58-3,7689-02-3,32975-45-4,52152-79-1,2912-09-6)

Guidance literature:

With hydrogen; palladium(II) hydroxide; In methanol; ethyl acetate; at 23 ℃; under 10343.2 Torr;

DOI:10.1038/nature10232

Reference yield: 90.0%

5-oxo-aspidospermidine (477904-34-0) → (+)-aspidospermidine (7013-58-3,7689-02-3,32975-45-4,52152-79-1,2912-09-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1021/ja026357f

Reference yield: 83.0%

(+)-1,2-didehydroaspidospermidine (19751-76-9,56245-51-3,65377-84-6) → (+)-aspidospermidine (7013-58-3,7689-02-3,32975-45-4,52152-79-1,2912-09-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 12h; Reflux;

DOI:10.1021/acs.orglett.7b01292

upstream raw materials:

(+)-2,3-Didehydro-1-<(4-methoxyphenyl)sulfonyl>aspidospermidin-10-one

(3¹S,6aR,9aR)-6a-ethyloctahydro-1H-pyrrolo[3,2,1-ij]quinolin-9(2H)-one

phenylhydrazine

5-oxo-aspidospermidine

Downstream raw materials:

(+)-vincadifformine

(+)-1,2-didehydroaspidospermidine

(-)-N-acetylaspidospermidine

(-)-demethoxypalosine

Refernces

'Aromatic ring umpolung', a rapid access to the main core of several natural products

10.1016/j.tet.2010.03.096

The research explores a novel synthetic strategy for rapidly constructing the core structures of various natural products using the concept of aromatic ring umpolung. The purpose of this study is to develop a versatile and efficient method for synthesizing complex natural product cores by leveraging the reactivity inversion of aromatic rings, specifically through the formation of phenoxenium ions using hypervalent iodine reagents such as (diacetoxyiodo)benzene (DIB). The researchers demonstrate that these highly electrophilic intermediates can react with various nucleophiles, leading to a range of different cores found in natural products through oxidative processes. Key findings include the successful synthesis of tricyclic compounds via a formal [2+3] cycloaddition with furan, the oxidative addition of carbon-based nucleophiles to create quaternary carbon centers, and the development of an oxidative transposition process to generate highly functionalized cores. The study concludes that these methodologies offer rapid access to complex natural product cores, significantly reducing the number of synthetic steps required. This approach not only provides a powerful tool for the synthesis of natural products like panacene, mesembrine, and aspidospermidine but also opens up new strategic opportunities in chemical synthesis by transforming simple phenols into highly functionalized structures.