38848-26-9

Upstream product

• 38848-25-8 (±)-demethylcephalotaxinone 
• 77-76-9 2,2-dimethoxy-propane 
• 35667-11-9 5,8,9,10-tetrahydro-6H-1,3-dioxolo<4,5-h>pyrrolo<2,1-b><3>benzazepine 
• 6882-28-6 norhydrastinine 
• 149-73-5 trimethyl orthoformate 
• 35761-91-2 5-iodo-1-trimethylsilyl-1-pentyne 
• 1825-61-2 Trimethylmethoxysilane 
• 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 
• 38848-23-6 2-hydroxy-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 
• 38847-96-0 5,8,9,10-tetrahydro-[1,3]dioxolo[4',5':4,5]benzo[d]pyrrolo[1,2-a]azepin-6-one 
• 38847-95-9 1-(benzo[1,3]dioxol-5-yl-acetyl)-pyrrolidine-2-carbaldehyde 

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 
• 38750-57-1 (-)-Cephalotaxinone 
• 38848-21-4 (±)-cephalotaxine 

Relevant academic research and scientific papers

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.

ANALOGUES AND DERIVATIVES OF CEPHALOTAXINE AND METHODS FOR MAKING AND USING THE COMPOUNDS

Disclosed herein are embodiments of a compound having a Formula I, or a salt, solvate, N-oxide, prodrug, diastereomer or enantiomer thereof. Also disclosed are derivative compounds made from the compound of Formula I. Certain derivative compounds have a Formula V-2, or a salt, solvate, N-oxide, prodrug, diastereomer or enantiomer thereoAlso disclosed are method for making and using the disclosed compounds. Certain disclosed embodiments are useful for treating and/or preventing certain diseases and/or disorders, including proliferation diseases, such as leukemia.

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).

Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (±)-Cephalotaxine

A stereoselective N-iminium ion cyclization with allylsilane to construct vicinal quaternary-tertiary carbon centers was developed for the concise synthesis of (±)-cephalotaxine. The current strategy features a TiCl4-promoted cyclization and ring-closure metathesis to furnish the spiro-ring system. The stereochemical outcome in the N-acyliminium ion cyclization was rationalized by the stereoelectronic effect of the Z- or E-allylsilane. Two diastereomers arising from the cyclization were merged into the formal synthesis of (±)-cephalotaxine.

Total synthesis of the Cephalotaxus alkaloids dl-cephalotaxine, dl-11-hydroxycephalotaxine, and dl-drupacine

This paper reports the chemical details of our total synthesis of dl-cephalotaxine (1) and the completion of the first total synthesis of dl-11-hydroxycephalotaxine (3) and dl-drupacine (4). Key steps in the synthesis of dl-cephalotaxine include: (1) conj

Biosynthesis of the Cephalotaxus Alkaloids. Investigations of the Early and Late Stages of Cephalotaxine Biosynthesis

The biosynthesis of the alkaloid cephalotaxine (1) has been investigated by means of precursor incorporation experiments with Cephalotaxus harringtonia.It has been established that cephalotaxine is biosynthesized from one molecule each of tyrosine and phenylalanine in a manner consistent with the hypothesis that 1 is a modified 1-phenethyltetrahydroisoquinoline alkaloid.Incorporation experiments with - and phenylalanine have shown that one of the meta carbon atoms of phenylalanine is lost during the conversion of this amino acid into cephalotaxine.The remaining meta carbon atom is located at C-2 of the alkaloid.Cephalotaxine (1), cephalotaxinone (2), demethylcephalotaxinone (3), and demethylcephalotaxine (4) labeled with carbon-14 at C-3 have been synthesized.Incorporation experiments with these labeled alkaloids have established that cephalotaxine and cephalotaxinone are irreversibly demethylated in vivo.