27498-90-4

Basic information

• Product Name: (-)-Stemonine
• Synonyms: (1S,3aβ,10aα,10bα)-Decahydro-1α-methyl-8α-[(2S,4S)-tetrahydro-4-methyl-5-oxofuran-2-yl]-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-one;Stemonine【C17 alkaloid】
• CAS NO: 27498-90-4
• Molecular Formula: C17H25NO4
• Molecular Weight: 307.3847
• Mol File: 27498-90-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-Stemonine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Stemonine(27498-90-4)
• EPA Substance Registry System: (-)-Stemonine(27498-90-4)

Safety Data

• Hazardous Substances Data: 27498-90-4(Hazardous Substances Data)

Usage

General Description

(-)-Stemonine is a naturally occurring alkaloid found in the plant Stemona japonica. It is known for its insecticidal properties and has been used in traditional Chinese medicine for its antitussive and expectorant effects. Studies have also shown its potential as an anticancer agent, with its ability to inhibit the growth of cancer cells. (-)-Stemonine has been of interest to researchers for its bioactive properties and potential pharmaceutical applications, making it a subject of further investigation for its medicinal and agricultural uses.

Upstream product

• 794528-61-3 (1S,3aR,10aS,10bR)-1-methyloctahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione 
• 410535-69-2 (3aR,10aS,10bR)-octahydro-2H-furo[3,2-c]pyrrolo[1,2-a]azepine-2,8(1H)-dione 
• 609817-38-1 Methanesulfonic acid (Z)-(1R,7S)-1-{(1S,2R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-pentyl}-8-methoxymethoxy-7-methyl-oct-4-enyl ester 
• 609817-39-2 {(4R,5R,6S,12S)-(Z)-6-azido-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-enyloxymethyl}benzene 
• 609817-36-9 (Z)-(4R,5R,12S)-1-benzyloxy-4-(tert-butyldimethylsilanyloxy)-5-[(S)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-13-methoxymethoxy-12-methyltridec-9-en-6-one 

Relevant articles and documents

Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks

A unified total synthesis of stemoamide-type alkaloids is reported. Our synthetic approach features the chemoselective convergent assembly of five-membered building blocks via stemoamide as the common precursor to tetracyclic natural products. The synthesis consists of two successive coupling reactions of the three five-membered building blocks. The first coupling reaction is the vinylogous Michael addition/reduction sequence, which enables the gram-scale synthesis of stemoamide. The second coupling reaction is a chemoselective nucleophilic addition to stemoamide. While the lactone-selective nucleophilic addition to stemoamide affords saxorumamide and isosaxorumamide, the lactam-selective reductive nucleophilic addition leads to the formation of stemonine. Both chemoselective nucleophilic additions enable direct modification of stemoamide, resulting in highly concise and efficient total syntheses of the stemoamide-type alkaloids.

Tailored Synthesis of Skeletally Diverse Stemona Alkaloids through Chemoselective Dyotropic Rearrangements of β-Lactones

The collective synthesis of skeletally diverse Stemona alkaloids featuring tailored dyotropic rearrangements of β-lactones as key elements is described. Specifically, three typical 5/7/5 tricyclic skeletons associated with stemoamide, tuberostemospiroline and parvistemonine were first accessed through chemoselective dyotropic rearrangements of β-lactones involving alkyl, hydrogen, and aryl migration, respectively. By the rational manipulation of substrate structures and reaction conditions, these dyotropic rearrangements proceeded with excellent efficiency, good chemoselectivity and high stereospecificity. Furthermore, several polycyclic Stemona alkaloids, including saxorumamide, isosaxorumamide, stemonine and bisdehydroneostemoninine, were obtained from the aforementioned tricyclic skeletons through late-stage derivatizations. A novel visible-light photoredox-catalyzed formal [3+2] cycloaddition was also developed, which offers a valuable tool for accessing oxaspirobutenolide and related scaffolds.