59633-82-8

Basic information

• Product Name: Axamide 3
• Synonyms: (-)-Axamide 3;Axamide 3
• CAS NO: 59633-82-8
• Molecular Formula: C₁₆H₂₇NO
• Molecular Weight: 249.39
• Mol File: 59633-82-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Axamide 3(CAS DataBase Reference)
• NIST Chemistry Reference: Axamide 3(59633-82-8)
• EPA Substance Registry System: Axamide 3(59633-82-8)

Safety Data

• Hazardous Substances Data: 59633-82-8(Hazardous Substances Data)

Upstream product

• 1197389-96-0 C₁₇H₂₉NO₂ 
• 2258-42-6 formyl acetic anhydride 
• 509078-99-3 (5S,6R,7S,10S)-7-isopropyl-2,10-dimethylspiro[4.5]dec-1-en-6-ylamine 
• 109-94-4 formic acid ethyl ester 

Relevant articles and documents

New spirocyclic sesquiterpenes from the marine sponge Geodia exigua

Three new spirocyclic sesquiterpenes designated exiguamide (1), exicarbamate (2) and exigurin (3), together with (-)-10-epi-axisonitrile-3 (4), have been isolated from the marine sponge Geodia exigua. All four compounds possess the spiro[4.5]decene skeleton and their structures were determined on the basis of spectroscopic data. The structure of 1 was confirmed by X-ray crystallographic analysis and the absolute configuration was determined by applying the modified Mosher's method on its amine derivative. Exiguamide (1) inhibited cell fate specification during sea urchin embryogenesis at a minimum inhibitory concentration of 0.4μM.

First enantioselective synthesis of exiguamide, a nitrogen-containing spirocyclic sesquiterpene isolated from the marine sponge Geodia exigua

(+)-Exiguamide is a nitrogen-containing spirocyclic sesquiterpene isolated from the marine sponge Geodia exigua. This study aims to report the first synthesis of both enantiomers of exiguamide, featuring the stereoselective intramolecular cyclopropanation

Total synthesis of exigurin: The Ugi reaction in a hypothetical biosynthesis of natural products

The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.

Stereocontrolled total synthesis of antimalarial (+)-axisonitrile-3

Here we describe the total synthesis of the antimalarial sesquiterpene, (+)-axisonitrile-3. Three key features of this synthesis are: (i) non-Evans syn-aldol reaction of an isovaleric acid derivative bearing a chiral oxazolidinethione and crotonaldehyde w