The first total synthesis of (−)-mitragynine, an analgesic indole alkaloid in mitragyna speciosa
Starting from an optically pure alcohol, ( R)-( 3), which was prepared by enzymatic hydrolysis of the racemic acetate ( 2) or enantioselective reduction of the ketone derivative ( 4), the chiral total synthesis of mitragynine ( 1), a major corynanthe-type indole alkaloid having an analgesic effect i...
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| Published in: | Tetrahedron letters Vol. 36; no. 51; pp. 9337 - 9340 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
18-12-1995
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| Abstract | Starting from an optically pure alcohol, (
R)-(
3), which was prepared by enzymatic hydrolysis of the racemic acetate (
2) or enantioselective reduction of the ketone derivative (
4), the chiral total synthesis of mitragynine (
1), a major corynanthe-type indole alkaloid having an analgesic effect in
Mitragyna speciosa, was accomplished. |
|---|---|
| AbstractList | Starting from an optically pure alcohol, (
R)-(
3), which was prepared by enzymatic hydrolysis of the racemic acetate (
2) or enantioselective reduction of the ketone derivative (
4), the chiral total synthesis of mitragynine (
1), a major corynanthe-type indole alkaloid having an analgesic effect in
Mitragyna speciosa, was accomplished. |
| Author | Ohbayashi, Satoshi Kitajima, Mariko Aimi, Norio Maeda, Moriyoshi Takayama, Hiromitsu Sakai, Shin-ichiro |
| Author_xml | – sequence: 1 givenname: Hiromitsu surname: Takayama fullname: Takayama, Hiromitsu – sequence: 2 givenname: Moriyoshi surname: Maeda fullname: Maeda, Moriyoshi – sequence: 3 givenname: Satoshi surname: Ohbayashi fullname: Ohbayashi, Satoshi – sequence: 4 givenname: Mariko surname: Kitajima fullname: Kitajima, Mariko – sequence: 5 givenname: Shin-ichiro surname: Sakai fullname: Sakai, Shin-ichiro – sequence: 6 givenname: Norio surname: Aimi fullname: Aimi, Norio |
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| Cites_doi | 10.1021/ja00516a042 10.1016/S0957-4166(00)82175-8 10.1016/S0040-4039(01)97749-4 10.1016/S0040-4020(01)83323-8 10.1002/cber.19761091209 10.1016/0378-8741(88)90121-3 10.1016/S0040-4039(00)78505-4 10.1055/s-2006-959578 10.1021/ja00259a075 10.3987/COM-91-5922 10.1016/S0040-4020(01)87031-9 |
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| References | Takayama, Yamamoto, Kurihara, Kitajima, Aimi, Mao, Sakai (bib3) 1994; 35 Rackur, Stahl, Walkowiak, Winterfeldt (bib5) 1976; 109 Lee, Trager, Beckelt (bib16) 1967; 23 bib14 bib15 Uskokovic, Lewis, Partridge, Despreaux, Pruess (bib8) 1979; 101 bib13 bib10 Seemayer, Schneider (bib12) 1992; 3 Jansen, Prast (bib1) 1988; 23 bib9 Ponglux, Wongseripipatana, Takayama, Kikuchi, Kurihara, Kitajima, Aimi, Sakai (bib2) 1994; 60 Ziegler, Sweeny (bib4) 1969 Tirkkonen, Miettinen, Salo, Jokela, Lounasmaa (bib7) 1994; 50 Lounasmaa, Jokela, Tirkkonen, Miettinen, Halonen (bib6) 1992; 34 Corey, Bakshi, Shibata, Chen, Singh (bib11) 1987; 109 Ponglux (10.1016/0040-4039(95)02022-H_bib2) 1994; 60 Lee (10.1016/0040-4039(95)02022-H_bib16) 1967; 23 Tirkkonen (10.1016/0040-4039(95)02022-H_bib7) 1994; 50 Jansen (10.1016/0040-4039(95)02022-H_bib1) 1988; 23 Corey (10.1016/0040-4039(95)02022-H_bib11) 1987; 109 Ziegler (10.1016/0040-4039(95)02022-H_bib4) 1969 Rackur (10.1016/0040-4039(95)02022-H_bib5) 1976; 109 Lounasmaa (10.1016/0040-4039(95)02022-H_bib6) 1992; 34 Takayama (10.1016/0040-4039(95)02022-H_bib3) 1994; 35 Uskokovic (10.1016/0040-4039(95)02022-H_bib8) 1979; 101 Seemayer (10.1016/0040-4039(95)02022-H_bib12) 1992; 3 |
| References_xml | – volume: 101 start-page: 6742 year: 1979 ident: bib8 publication-title: J. Am. Chem. Soc. contributor: fullname: Pruess – volume: 35 start-page: 8813 year: 1994 ident: bib3 publication-title: Tetrahedron Lett. contributor: fullname: Sakai – ident: bib14 – ident: bib15 – volume: 50 start-page: 3537 year: 1994 ident: bib7 publication-title: Tetrahedron contributor: fullname: Lounasmaa – volume: 23 start-page: 375 year: 1967 ident: bib16 publication-title: Tetrahedron contributor: fullname: Beckelt – volume: 60 start-page: 580 year: 1994 ident: bib2 publication-title: Planta Med. contributor: fullname: Sakai – start-page: 1097 year: 1969 ident: bib4 publication-title: Tetrahedron Lett. contributor: fullname: Sweeny – ident: bib9 – volume: 109 start-page: 3817 year: 1976 ident: bib5 publication-title: Chem. Ber. contributor: fullname: Winterfeldt – ident: bib10 – ident: bib13 – volume: 23 start-page: 115 year: 1988 ident: bib1 publication-title: J. Ethnopharmacol. contributor: fullname: Prast – volume: 34 start-page: 321 year: 1992 ident: bib6 publication-title: Heterocycles contributor: fullname: Halonen – volume: 3 start-page: 827 year: 1992 ident: bib12 publication-title: Tetrahedron: Asymmetry contributor: fullname: Schneider – volume: 109 start-page: 7925 year: 1987 ident: bib11 publication-title: J. Am. Chem. Soc. contributor: fullname: Singh – volume: 101 start-page: 6742 year: 1979 ident: 10.1016/0040-4039(95)02022-H_bib8 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00516a042 contributor: fullname: Uskokovic – volume: 3 start-page: 827 year: 1992 ident: 10.1016/0040-4039(95)02022-H_bib12 publication-title: Tetrahedron: Asymmetry doi: 10.1016/S0957-4166(00)82175-8 contributor: fullname: Seemayer – start-page: 1097 year: 1969 ident: 10.1016/0040-4039(95)02022-H_bib4 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)97749-4 contributor: fullname: Ziegler – volume: 23 start-page: 375 year: 1967 ident: 10.1016/0040-4039(95)02022-H_bib16 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)83323-8 contributor: fullname: Lee – volume: 109 start-page: 3817 year: 1976 ident: 10.1016/0040-4039(95)02022-H_bib5 publication-title: Chem. Ber. doi: 10.1002/cber.19761091209 contributor: fullname: Rackur – volume: 23 start-page: 115 year: 1988 ident: 10.1016/0040-4039(95)02022-H_bib1 publication-title: J. Ethnopharmacol. doi: 10.1016/0378-8741(88)90121-3 contributor: fullname: Jansen – volume: 35 start-page: 8813 year: 1994 ident: 10.1016/0040-4039(95)02022-H_bib3 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)78505-4 contributor: fullname: Takayama – volume: 60 start-page: 580 year: 1994 ident: 10.1016/0040-4039(95)02022-H_bib2 publication-title: Planta Med. doi: 10.1055/s-2006-959578 contributor: fullname: Ponglux – volume: 109 start-page: 7925 year: 1987 ident: 10.1016/0040-4039(95)02022-H_bib11 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00259a075 contributor: fullname: Corey – volume: 34 start-page: 321 year: 1992 ident: 10.1016/0040-4039(95)02022-H_bib6 publication-title: Heterocycles doi: 10.3987/COM-91-5922 contributor: fullname: Lounasmaa – volume: 50 start-page: 3537 year: 1994 ident: 10.1016/0040-4039(95)02022-H_bib7 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)87031-9 contributor: fullname: Tirkkonen |
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| Title | The first total synthesis of (−)-mitragynine, an analgesic indole alkaloid in mitragyna speciosa |
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