91444-81-4

Basic information

• Product Name: C₂₁H₂₈O₃
• CAS NO: 91444-81-4
• Molecular Weight: 328.452
• Mol File: 91444-81-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₁H₂₈O₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₁H₂₈O₃(91444-81-4)
• EPA Substance Registry System: C₂₁H₂₈O₃(91444-81-4)

Safety Data

• Hazardous Substances Data: 91444-81-4(Hazardous Substances Data)

Upstream product

• 61950-54-7 (8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene 
• 100-39-0 benzyl bromide 
• 91444-85-8 (S)-8a'-methyl-5'-(phenylthiomethyl)-3',4',8',8a'-tetrahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one 

Relevant articles and documents

An Efficient Approach to Chiral, Nonracemic trans-Decahydro-5,8a-dimethyl-1,6-naphthalenedione Derivatives: Total Synthesis of (+)-Pallescensin A

The syntheses of of six chiral, nonracemic trans-decahydro-5,8a-dimethyl-1,6-naphthalenedione derivatives 1a-f are described.The approach calls for the reductive alkylation of enone 4 readily available from (+)-Wieland-Miescher ketone (5) via chemoselective ketalization on the C(8)-carbonyl followed by application of the Kirk-Petrow (phenylthio)methylation protocol.Yields for reactive electrophiles are in the range of 70-85percent.To demonstrate the utility of this method, we record here a nine-step total synthesis of (+)-pallescensin A (8); the overall yield from enone 4 was 13percent.