1354568-46-9

Upstream product

• 1354568-15-2 C₁₈H₂₁NO₄ 

Downstream Products

• 1354568-68-5 C₁₆H₂₅NO 
• 473-99-4 eburnamine 
• 4880-88-0 vinburnine 
• 1617-90-9 vincamin 
• 35226-43-8 (3α,16α)-D-homoeburnamonine-14,15-dione 

Relevant academic research and scientific papers

Total Syntheses of rac- and (+)-Goniomitine

Concise total syntheses of rac- and (+)-goniomitine were developed. The cyanide-catalyzed imino-Stetter reaction of an aldimine, derived from ethyl 2-aminocinnamate and either rac- or (S)-α,β-unsaturated aldehyde bearing a δ-valerolactam at the β-position

Enantioselective total synthesis of (+)-vincamine

A catalytic asymmetric total synthesis of (+)-vincamine is presented. Key features of the synthesis include a Pd-catalyzed enantioselective decarboxylative allylation to form the C20 quaternary stereogenic center and a stereoselective iminium reduction to install the critical cis-C20/C21 relative stereochemisty.

ASYMMETRIC CATALYTIC DECARBOXYLATIVE ALKYL ALKYLATION USING LOW CATALYST CONCENTRATIONS AND A ROBUST PRECATALYST

This invention provides efficient and scalable enantioselective methods that yield 2-alkyl-2-allylcycloalkyanone compounds with quaternary stereogenic centers. Methods include the method for the preparation of a compound of formula (I): comprising treatin

An Efficient Protocol for the Palladium-Catalyzed Asymmetric Decarboxylative Allylic Alkylation Using Low Palladium Concentrations and a Palladium(II) Precatalyst

Enantioselective catalytic allylic alkylation for the synthesis of 2-alkyl-2-allylcycloalkanones and 3,3-disubstituted pyrrolidinones, piperidinones and piperazinones has been previously reported by our laboratory. The efficient construction of chiral all

Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation

Pd-catalyzed enantioselective alkylation in conjunction with further synthetic elaboration enables the formal total syntheses of a number of "classic" natural product target molecules. This publication highlights recent methods for setting quaternary and tetrasubstituted tertiary carbon stereocenters to address the synthetic hurdles encountered over many decades across multiple compound classes spanning carbohydrate derivatives, terpenes, and alkaloids. These enantioselective methods will impact both academic and industrial settings, where the synthesis of stereogenic quaternary carbons is a continuing challenge.

QUATERNARY HETEROATOM CONTAINING COMPOUNDS

A compound useful as a building block for the manufacture of various compounds is represented by Formula A or D. In Formula A and D, z is 0 or 1; Q is a heteroatom; Rl through R1 1 and Ra through Rf are each independently hydrogen, a substituted or unsubstituted hydrocarbyl group, a substituted or unsubstituted heteroatom containing hydrocarbyl group, or a functional group; d, e and f are each independently 0 or greater; each of A, B and D is independently a carbon atom or a heteroatom; and two or more of R1 though R1 1, Ra through Rf and Y optionally combine to form a ring. In some embodiments, R8 and R9 combine to form a carbonyl group. In some embodiments, R2 and Y combine to form a ring with the Q atom. In some embodiments, the ring includes at least one double bond.

Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams

The enantioselective synthesis of nitrogen-containing heterocycles (N-heterocycles) represents a substantial chemical research effort and resonates across numerous disciplines, including the total synthesis of natural products and medicinal chemistry. In