38750-57-1

Basic information

• Product Name: 3-Deoxy-3-oxocephalotaxine
• Synonyms: 3-Deoxy-3-oxocephalotaxine
• CAS NO: 38750-57-1
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.34776
• Mol File: 38750-57-1.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Deoxy-3-oxocephalotaxine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Deoxy-3-oxocephalotaxine(38750-57-1)
• EPA Substance Registry System: 3-Deoxy-3-oxocephalotaxine(38750-57-1)

Safety Data

• Hazardous Substances Data: 38750-57-1(Hazardous Substances Data)

Upstream product

• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 62681-68-9 (E)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime 
• 38847-95-9 1-(benzo[1,3]dioxol-5-yl-acetyl)-pyrrolidine-2-carbaldehyde 
• 24316-19-6 cephalotaxine 
• 35761-91-2 5-iodo-1-trimethylsilyl-1-pentyne 
• 149-73-5 trimethyl orthoformate 
• 6882-28-6 norhydrastinine 
• 1825-61-2 Trimethylmethoxysilane 
• 38848-25-8 (±)-demethylcephalotaxinone 
• 35667-11-9 5,8,9,10-tetrahydro-6H-1,3-dioxolo<4,5-h>pyrrolo<2,1-b><3>benzazepine 
• 38848-22-5 2-acetoxy-1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propan-1-one 
• 38848-24-7 1-(5,8,9,10-tetrahydro-6H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepin-11-yl)-propane-1,2-dione 

Downstream Products

• 1040272-38-5 (1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-4-oxooxetane-2-carboxylate 
• 1040272-14-7 1-((1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl) 4-methyl (R)-2-((E)-4-(benzyloxy)-4-methylpent-2-en-1-yl)-2-hydroxysuccinate 
• 26833-87-4 homoharringtonine 
• 24316-19-6 cephalotaxine 
• 36804-95-2 deoxyharringtonine 
• 38848-21-4 (±)-cephalotaxine 

Relevant articles and documents

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Gold(I)-Catalyzed Cyclization-3-Aza-Cope-Mannich Cascade and Its Application to the Synthesis of Cephalotaxine

The discovery of a new gold(I)-catalyzed cascade reaction involving cyclization onto a vinylammonium, 3-aza-Cope rearrangement, and Mannich cyclization is reported. A variety of fused nitrogen heterocycles were prepared from simple cyclic tertiary amines using 1-5 mol % of a AuCl(PPh3)/Ag[C5(CN)5] cocatalyst system. The developed reaction was used in a study aimed at synthesizing cephalotaxine. A five-step operation from norhydrastinine provided demethylcephalotaxinone in 39.1% overall yield, which was transformed to (-)-cephalotaxine in two steps.

Total Synthesis of (?)-Cephalotaxine and (?)-Homoharringtonine via Furan Oxidation–Transannular Mannich Cyclization

Homoharringtonine and its congener cephalotaxine were synthesized. Oxidative ring-opening of a furan unveils an amine-tethered dicarbonyl, which undergoes spontaneous transannular Mannich cyclization. The cascade builds the full cephalotaxine substructure in a single operation in 60 % yield. A Noyori reduction enabled synthesis of the title compounds with excellent enantioselectivity (krel=278).

CEPHALOTAXUS ESTERS, METHODS OF SYNTHESIS, AND USES THEREOF

The present invention provides novel cephalotaxus esters, syntheses thereof, and intermediates thereto. The invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of using said compounds or compositions in the treatment of proliferative diseases (e.g., benign neoplasm, cancer, inflammatory disease, autoimmune disease, diabetic retinopathy) and infectious disease. The invention further provides methods of using said compounds or compositions in the treatment of multidrug resistant cancer.