1151764-22-5

Upstream product

• 79328-85-1 N-benzyloxycarbonyl-1,2-dihydropyridine 
• 107-02-8 acrolein 
• 110-86-1 pyridine 
• 501-53-1 benzyl chloroformate 
• 1253521-29-7 exo/endo-benzyl 7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate 

Relevant academic research and scientific papers

A practical synthesis of (-)-oseltamivir

(Chemical Equation Presented) Keep it simple: Still in hot demand, the influenza drug (-)-oseltamivir phosphate (tamiflu; see scheme) has now been synthesized from pyridine by using inexpensive reagents. A strict minimum of purification steps are required in a synthetic route which features an asymmetric Diels-Alder reaction, a bromolactonization, a Hofmann rearrangement, and a domino transformation of a bicyclo[2.2.2] system into an aziridine intermediate.

Enantioselective Formal Total Synthesis of (-)-Quinagolide

The enantioselective formal total synthesis of (-)-quinagolide has been accomplished in a linear sequence of 8 purification steps from pyridine. The key steps are (a) organocatalyzed Diels-Alder reaction for fixing all three stereocenters on piperidine ri

Enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using β-amino alcohol organocatalyst

(Chemical Equation Presented) The enantioselective Diels-Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active β-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient syntheti

Chiral primary amino silyl ether organocatalyst for the enantioselective diels-alder reaction of 1,2-dihydropyridines with aldehydes

The enantioselective Diels-Alder reactions of 1,2-dihydropyridines with acroleins using a chiral primary amino silyl ether organocatalyst afforded chiral isoquinuclidines with good chemical yields and excellent enantioselectivities (up to 70% and up to 99

Asymmetric total synthesis of (+)-luciduline: Toward a general approach to related lycopodium alkaloids

As part of a research program directed toward the synthesis of Lycopodium alkaloids, a multigram scale asymmetric synthesis of intermediate 11 was achieved in 11 steps from pyridine (17). In addition to our alkene metathesis strategy, a key feature of thi

A highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate

An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1

A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine

Enantioselective Diels-Alder reactions of 1,2-dihydropyridines with acroleins using a novel chiral oxazolidine organocatalyst afforded chiral isoquinuclidines that is an efficient synthetic intermediate of oseltamivir, with fairly good chemical yield and

ISOQUINUCLIDINE DERIVATIVE AND METHOD FOR PRODUCING 1-CYCLOHEXENE-1-CARBOXYLIC ACID DERIVATIVE BY USING THE SAME

The present invention provides an isoquinuclidine derivative which can be used to easily synthesize oseltamivir or an analog thereof. In particular, the present invention provides an isoquinuclidine derivative represented by the following formula (1) or an enantiomer thereof: wherein in the formula (1), A represents a protective group for the nitrogen atom; R1 to R1 each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom; and X represents a halogen atom.

A practical synthesis of (-)-oseltamivir

Oseltamivir phosphate (Tamiflu) is a potent inhibitor of neuraminidase, and is used worldwide as a drug for type A or B influenza. The industrial synthesis of oseltamivir uses shikimic acid as a starting material, but the price fluctuates, depending on the supply of star anise. We have developed a practical synthesis of oseltamivir from pyridine, which features an asymmetric Diels-Alder reaction of dihydropyridine using MacMillan's catalyst, a bromolactonization, Hofmann rearrangement with PhI(OAc)2, and a domino transformation of the bicyclo[2.2.2] system into an aziridine compound.