61273-75-4

Usage

Uses

Used in Pharmaceutical Industry:
(4aS,6S,6aR,6bS,10aS)-6-hydroxy-3,9-dimethyl-4,4a,5,6,6a,6b,7,8,9,10,10a,11-dodecahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one is used as a potential pharmaceutical agent for its unique molecular structure and functional groups, which may contribute to specific biological activities and therapeutic effects.
Used in Research and Development:
In the field of organic chemistry and medicinal chemistry, (4aS,6S,6aR,6bS,10aS)-6-hydroxy-3,9-dimethyl-4,4a,5,6,6a,6b,7,8,9,10,10a,11-dodecahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one is used as a subject of interest for research and development. Its complex structure and potential reactivity due to the presence of the hydroxy group and other functional groups make it a valuable target for exploring new chemical reactions and biological interactions.

Upstream product

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

Downstream Products

• 73885-47-9 (+)-magellaninone 
• 73885-49-1 (4aR)-2c,3c-epoxy-6c-hydroxy-3t,9-dimethyl-(4ar,6at,6bc,10ac,11atC¹)-tetradecahydro-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one 

Relevant academic research and scientific papers

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.