391277-76-2

Basic information

• Product Name: 2-Oxazolidinone, 3-(3-hydroxy-1-oxo-4-pentenyl)-4-(phenylmethyl)-, (4S)-
• CAS NO: 391277-76-2
• Molecular Formula: C15H17NO4
• Molecular Weight: 275.304
• Mol File: 391277-76-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 3-(3-hydroxy-1-oxo-4-pentenyl)-4-(phenylmethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 3-(3-hydroxy-1-oxo-4-pentenyl)-4-(phenylmethyl)-, (4S)-(391277-76-2)
• EPA Substance Registry System: 2-Oxazolidinone, 3-(3-hydroxy-1-oxo-4-pentenyl)-4-(phenylmethyl)-, (4S)-(391277-76-2)

Safety Data

• Hazardous Substances Data: 391277-76-2(Hazardous Substances Data)

Upstream product

• 132836-66-9 (S)-3-acetyl-4-benzyloxazolidin-2-one 
• 107-02-8 acrolein 

Relevant articles and documents

Enantioselective synthesis of the antiinflammatory agent (-)-acanthoic acid

An enantioselective synthesis of the potent antiinflammatory agent (-)-acanthoic acid (1) is described. The successful strategy departs from (-)-Wieland-Miescher ketone (10), which is readily available in both enantiomeric forms and constitutes the starting point toward a fully functionalized AB ring system of 1. Conditions were developed for a regioselective double alkylation at the C4 center of the A ring, which produced compound 32 as a single stereoisomer. Construction of the C ring of 1 was accomplished via a Diels-Alder reaction between sulfur-containing diene 43 and methacrolein (36), which after desulfurization and further functionalization yielded synthetic acanthoic acid. The described synthesis confirms the proposed stereochemistry of the natural product and represents a fully stereocontrolled entry into an underexplored class of biologically active diterpenes.