Microflow photo-radical reaction using a compact light source: application to the Barton reaction leading to a key intermediate for myriceric acid A
Sugimoto, A; Fukuyama, T; Sumino, Y; Takagi, M; Ryu, I
| HERO ID | 620346 |
|---|---|
| In Press | No |
| Year | 2009 |
| Title | Microflow photo-radical reaction using a compact light source: application to the Barton reaction leading to a key intermediate for myriceric acid A |
| Authors | Sugimoto, A; Fukuyama, T; Sumino, Y; Takagi, M; Ryu, I |
| Journal | Tetrahedron |
| Volume | 65 |
| Issue | 8 |
| Page Numbers | 1593-1598 |
| Abstract | Abstract: The Barton reaction (nitrite photolysis) of a steroidal substrate 1, to give 2, a key intermediate for the synthesis of myriceric acid A, an endothelin receptor antagonist, was successfully carried out in a continuous microflow system using a Pyrex glass-covered stainless-steel microreactor having a one lane microchannel (Type A: 1000μm width, 107μm depth, 2.2m length). We found that using a low-power black light (peak wavelength: 352nm) and UV-LED light (peak wavelength: 365nm) as the light source will suffice for the Barton reaction, creating a compact energy-saving photo-microreaction system. A multi-gram-scale production was attained using a multi-lane microreactor (Type B: 1000μm width, 500μm depth, 0.5m length, 16 lanes) in conjunction with a black light. [Copyright 2009 Elsevier] Copyright of Tetrahedron is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts) |
| Doi | 10.1016/j.tet.2008.12.063 |
| Wosid | WOS:000263276000007 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | FREE radical reactions; LIGHT sources; CHEMICAL reactions; INTERMEDIATES (Chemistry); PHOTOCHEMISTRY; ORGANIC compounds -- Synthesis; MICROREACTORS |
| Is Qa | No |