130695-86-2

Upstream product

• 106681-33-8 rac-(5,6,7,8-tetrahydroindolizin-8-yl)methanol 
• 868366-91-0 1,2,3,5,6,7-hexahydroindolizine-8-carbaldehyde 
• 130604-92-1 ethyl (8S*,8aS*)-octahydroindolizine-8-carboxylate 
• 478797-09-0 8-methylene-octahydro-indolizine 
• 478797-14-7 tert-butyl 2-(5-chloropent-1-en-2-yl)pyrrolidine-1-carboxylate 
• 478797-08-9 2-[1-(3-methanesulfonyloxy-propyl)-vinyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 40134-18-7 methyl 2-chloropyridine-3-carboxylate 
• 92721-45-4 1-(pent-4-en-1-yl)pyrrolidine-2,5-dione 

Downstream Products

• 111975-29-2 (+/-)-tashiromine 

Relevant academic research and scientific papers

Br?nsted acid-mediated annulations of pyrroles featuring N-tethered α,β-unsaturated ketones and esters: Total syntheses of (±)-tashiromine and (±)-indolizidine 209I

This study provides the first report of the construction of tetrahydroindolizines and tetrahydropyrrolo[1,2-a]azepines via Br?nsted acid-mediated annulation of pyrroles featuring N-tethered α,β-unsaturated esters. In addition, the Br?nsted acid-catalyzed cyclization of pyrroles featuring pendant α,β-unsaturated ketones was applied to complete total syntheses of the indolizidine alkaloids (±)-tashiromine and (±)-indolizidine 209I.

Activating Imides with Triflic Acid: A General Intramolecular Aldol Condensation Strategy Toward Indolizidine, Quinolizidine, and Valmerin Alkaloids

A simple, inexpensive, step economic, and highly modular synthetic strategy to access izidine alkaloids is described. The key step is a TfOH-promoted intramolecular aldol condensation between enol and cyclic imide moieties. This cyclization strategy can be employed within an aza-Robinson annulation framework and represents a general tool to build fused bicyclic amines. To illustrate the power of this method, we describe the preparation of (±)-coniceine, (±)-quinolizidine, (±)-tashiromine, (±)-epilupinine, and the core of (±)-valmerins.

A Concise Asymmetric Total Synthesis of (+)-Epilupinine

Asymmetric total synthesis of (+)-epilupinine was achieved in just three steps using only commercially available common reagents. The total synthesis involved alkylations of N-nosylamide, ozone oxidation, and sequential reactions of the removal of the nosyl group, intramolecular dehydrative condensation, intramolecular Mannich reaction catalyzed by l-proline, and a reduction.

Rhodium-Catalyzed Domino Hydroformylation/Double-Cyclization Reaction of Arylacetylenecarboxamides: Diastereoselectivity Studies and Application in the Synthesis of 1-Azabicyclo[x.y.0]alkanes

A domino method for the rapid syntheses of 1-azabicyclo[x.y.0]alkane scaffolds, such as indolizidines, quinolizidines, decahydropyridoazepines, and their derivatives, has been developed. This strategy involved a rhodium-catalyzed hydroformylation of allyl

New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates

The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.

Novel stereocontrolled syntheses of tashiromine and epitashiromine

A novel stereocontrolled approach has been developed for the syntheses of tashiromine and epitashiromine alkaloids from cyclooctene β-amino acids. The synthetic concept is based on the azetidinone opening of a bicyclic β-lactam, followed by oxidative ring

Electroreductive intramolecular coupling of aliphatic cyclic imides with α,β-unsaturated esters and ketones: Unusual methyl-alkoxy exchange in silyl ketene acetals

The electroreductive intramolecular coupling of aliphatic cyclic imides with α,β-unsaturated esters in the presence of chlorotrimethylsilane and subsequent desilylation with TBAF gave five- and six-membered cyclized esters and one-carbon elongated methyl

Iminium ion cascade reactions: stereoselective synthesis of quinolizidines and indolizidines

A novel iminium ion cascade reaction has been developed that allows for the stereoselective synthesis of a variety of substituted aza-fused bicycles. The combination of amino allylsilanes and aldehydes (or ketones) was used to synthesize a number of quino

Concise syntheses of substituted indolizidine alkaloids via cyclization based on α-sulfinyl carbanions: preparation of (±)-indolizidines 167B and 209D, their epimers, and (±)-tashiromine

(±)-Indolizidines 167B and 209D, their epimers and (±)-tashiromine have been successfully synthesized, starting from simple γ- or α-lactams. The strategy involves the cyclization of α-sulfinyl carbanion onto the carbonyl group of the lactam ring as the ke

Intramolecular additions of various π-nucleophiles to chemoselectively activated amides and application to the synthesis of (±)-tashiromine

Vilsmeier-Haack type cyclizations proved to be particularly efficient for generating parts of the polycyclic cores of many alkaloids, although only monocyclizations have so far been reported. With the goal of rapidly and efficiently constructing polycycli