European journal of organic chemistry

Enantioselective Synthesis of (+)??(S)??Laudanosine and (–)??(S)??Xylopinine

D Mujahidin, S Doye

Index: Mujahidin, Didin; Doye, Sven European Journal of Organic Chemistry, 2005 , # 13 p. 2689 - 2693

Full Text: HTML

Citation Number: 41

Abstract

Abstract The study presents a new pathway for the enantioselective synthesis of benzylisoquinoline alkaloids. The key steps of the synthesis of (+)-(S)-laudanosine (1) and (– )-(S)-xylopinine (2) are a Sonogashira coupling that builds up the C1–C8a bond of the benzylisoquinoline skeleton, an intramolecular Ti-catalyzed hydroamination of an alkyne, and a subsequent enantioselective imine reduction according to Noyori's protocol.(© ...

 Related Synthetic Route
Formaldehyde Structure

50-00-0

Formaldehyde

1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline Structure

6957-27-3

1-[(3,4-Dimetho...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

(-)-laudanosine Structure

85-63-2

(-)-laudanosine

3,4-Dimethoxyphenethylamine Structure

120-20-7

3,4-Dimethoxyph...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

((3,4-dimethoxyphenyl)ethynyl)trimethylsilane Structure

863132-17-6

((3,4-dimethoxy...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

2-(2-((3,4-dimethoxyphenyl)ethynyl)-4,5-dimethoxyphenyl)ethan-1-amine Structure

863132-09-6

2-(2-((3,4-dime...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

N-(2-((3,4-dimethoxyphenyl)ethynyl)-4,5-dimethoxyphenethyl)-2,2,2-trifluoroacetamide Structure

863132-19-8

N-(2-((3,4-dime...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

1,2-Dimethoxybenzene Structure

91-16-7

1,2-Dimethoxybenzene

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

4-Ethynyl-1,2-dimethoxybenzene Structure

4302-52-7

4-Ethynyl-1,2-d...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

4-Iodo-1,2-dimethoxybenzene Structure

5460-32-2

4-Iodo-1,2-dime...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide Structure

13230-71-2

N-[2-(3,4-dimet...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

2,2,2-trifluoro-N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]acetamide Structure

154138-43-9

2,2,2-trifluoro...

~%

(+)-Laudanosine Structure

2688-77-9

(+)-Laudanosine

((3,4-dimethoxyphenyl)ethynyl)trimethylsilane Structure

863132-17-6

((3,4-dimethoxy...

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

2-(2-((3,4-dimethoxyphenyl)ethynyl)-4,5-dimethoxyphenyl)ethan-1-amine Structure

863132-09-6

2-(2-((3,4-dime...

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

N-(2-((3,4-dimethoxyphenyl)ethynyl)-4,5-dimethoxyphenethyl)-2,2,2-trifluoroacetamide Structure

863132-19-8

N-(2-((3,4-dime...

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

1,2-Dimethoxybenzene Structure

91-16-7

1,2-Dimethoxybenzene

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

4-Ethynyl-1,2-dimethoxybenzene Structure

4302-52-7

4-Ethynyl-1,2-d...

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

4-Iodo-1,2-dimethoxybenzene Structure

5460-32-2

4-Iodo-1,2-dime...

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide Structure

13230-71-2

N-[2-(3,4-dimet...

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

2,2,2-trifluoro-N-[2-(2-iodo-4,5-dimethoxyphenyl)ethyl]acetamide Structure

154138-43-9

2,2,2-trifluoro...

~%

(R)-(+)-Tetrahydropapaverine Structure

50896-90-7

(R)-(+)-Tetrahy...

2-(2-((3,4-dimethoxyphenyl)ethynyl)-4,5-dimethoxyphenyl)ethan-1-amine Structure

863132-09-6

2-(2-((3,4-dime...

~98%

1-[(3,4-Dimethoxyphenyl)methyl]-3,4-dihydro-6,7-dimethoxyisoquinoline Structure

6957-27-3

1-[(3,4-Dimetho...

((3,4-dimethoxyphenyl)ethynyl)trimethylsilane Structure

863132-17-6

((3,4-dimethoxy...

~82%

4-Ethynyl-1,2-dimethoxybenzene Structure

4302-52-7

4-Ethynyl-1,2-d...

1,2-Dimethoxybenzene Structure

91-16-7

1,2-Dimethoxybenzene

~%

4-Ethynyl-1,2-dimethoxybenzene Structure

4302-52-7

4-Ethynyl-1,2-d...


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved