73885-47-9

Basic information

• Product Name: (4aS,6aR,6bS,10aS,11aS)-3,9-dimethyl-4a,5,6a,6b,7,8,9,10,10a,11-decahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridine-1,6(4H)-dione
• CAS NO: 73885-47-9
• Molecular Formula: C₁₇H₂₃NO₂
• Molecular Weight: 273.37
• Mol File: 73885-47-9.mol

Chemical Properties

• Boiling Point: 429.1°C at 760 mmHg
• Flash Point: 188.5°C
• Density: 1.18g/cm³
• Vapor Pressure: 1.43E-07mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: (4aS,6aR,6bS,10aS,11aS)-3,9-dimethyl-4a,5,6a,6b,7,8,9,10,10a,11-decahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridine-1,6(4H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,6aR,6bS,10aS,11aS)-3,9-dimethyl-4a,5,6a,6b,7,8,9,10,10a,11-decahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridine-1,6(4H)-dione(73885-47-9)
• EPA Substance Registry System: (4aS,6aR,6bS,10aS,11aS)-3,9-dimethyl-4a,5,6a,6b,7,8,9,10,10a,11-decahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridine-1,6(4H)-dione(73885-47-9)

Safety Data

• Hazardous Substances Data: 73885-47-9(Hazardous Substances Data)

Upstream product

• 61273-75-4 (-)-magellanine 
• 54307-74-3 (R)-5-methyl-cyclohex-2-enone 
• 147649-47-6 C⁽⁵⁾-epimagellanine 

Downstream Products

• 61273-75-4 (-)-magellanine 

Relevant articles and documents

Exceedingly Concise and Elegant Synthesis of (+)-Paniculatine, (-)-Magellanine, and (+)-Magellaninone

Starting from inexpensive (+)-pulegone as the chiral building block, a highly convergent synthesis of the unusual diquinane-based structures of (+)-paniculatine (1), (-)-magellanine (2), and (+)-magellaninone (3), has been achieved. This approach is based upon a tandem acylation-alkylation of ketoester 8 and palladium-catalyzed olefin insertion, oxidation, and hydrogenation for construction of the tetracyclic framework. This exceedingly concise strategy, requiring only 12-14 steps, is the shortest to date.

Stereoselective total syntheses of three Lycopodium alkaloids, (-)-magellanine, (+)-magellaninone, and (+)-paniculatine, based on two Pauson-Khand reactions

(Chemical Equation Presented) The total syntheses of (-)-magellanine, (+)-magellaninone, and (+)-paniculatine were completed from diethyl L-tartrate via the common intermediate in a stereoselective manner. The crucial steps in these syntheses involved two intramolecular Pauson-Khand reactions of enynes: the first Pauson-Khand reaction constructed the bicyclo[4.3.0] carbon framework, the corresponding A and B rings of these alkaloids in a highly stereoselective manner, whereas the second Pauson-Khand reaction stereoselectively produced the bicyclo[3.3.0]skeleton, which could be converted into the C and D rings of the target natural products.