Literature DB >> 17685530

Total synthesis of the opioid agonistic indole alkaloid mitragynine and the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol.

Jun Ma1, Wenyuan Yin, Hao Zhou, James M Cook.   

Abstract

An enantiospecific method for the synthesis of 4-methoxytryptophan has been developed via a regiospecific Larock heteroannulation and employed for the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol, as well as the total synthesis of the opioid agonistic alkaloid mitragynine. The asymmetric Pictet-Spengler reaction and a Ni(COD)2-mediated cyclization served as key steps.

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Year:  2007        PMID： 17685530      PMCID： PMC2526544          DOI： 10.1021/ol071220l

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  A New Indole Alkaloid, 7 alpha-Hydroxy-7H-mitragynine, from Mitragyna speciosa in Thailand.

Authors:  D Ponglux; S Wongseripipatana; H Takayama; M Kikuchi; M Kurihara; M Kitajima; N Aimi; S Sakai
Journal:  Planta Med       Date:  1994-12       Impact factor: 3.352

2.  Quaternary indole alkaloids from the stem bark of Strychnos guianensis.

Authors:  J Penelle; M Tits; P Christen; J Molgo; V Brandt; M Frédérich; L Angenot
Journal:  Phytochemistry       Date:  2000-04       Impact factor: 4.072

3.  An enantioselective total synthesis of (+)-geissoschizine.

Authors:  S F Martin; K X Chen; C T Eary
Journal:  Org Lett       Date:  1999-07-15       Impact factor: 6.005

4.  Total synthesis of the cyclic heptapeptide Argyrin B: a new potent inhibitor of T-cell independent antibody formation.

Authors:  Steven V Ley; Alain Priour; Christoph Heusser
Journal:  Org Lett       Date:  2002-03-07       Impact factor: 6.005

5.  Partial agonistic effect of 9-hydroxycorynantheidine on mu-opioid receptor in the guinea-pig ileum.

Authors:  Kenjiro Matsumoto; Hiromitsu Takayama; Hayato Ishikawa; Norio Aimi; Dhavadee Ponglux; Kazuo Watanabe; Syunji Horie
Journal:  Life Sci       Date:  2005-11-02       Impact factor: 5.037

6.  Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.

Authors:  Hiromitsu Takayama; Hayato Ishikawa; Mika Kurihara; Mariko Kitajima; Norio Aimi; Dhavadee Ponglux; Fumi Koyama; Kenjiro Matsumoto; Tomoyuki Moriyama; Leonard T Yamamoto; Kazuo Watanabe; Toshihiko Murayama; Syunji Horie
Journal:  J Med Chem       Date:  2002-04-25       Impact factor: 7.446

7.  Catalytic asymmetric synthesis of the central tryptophan residue of celogentin C.

Authors:  Steven L Castle; G S C Srikanth
Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

8.  Regiospecific, enantiospecific total synthesis of the alkoxy-substituted indole bases, 16-epi-N(a)-methylgardneral, 11-methoxyaffinisine, and 11-methoxymacroline as well as the indole alkaloids alstophylline and macralstonine.

Authors:  Xiaoxiang Liu; Jeffrey R Deschamp; James M Cook
Journal:  Org Lett       Date:  2002-10-03       Impact factor: 6.005

9.  Stereocontrolled total synthesis of (-)-vincamajinine and (-)-11-methoxy-17-epivincamajine.

Authors:  Jianming Yu; Xiangyu Z Wearing; James M Cook
Journal:  J Am Chem Soc       Date:  2004-02-11       Impact factor: 15.419

Review 10.  Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa.

Authors:  Hiromitsu Takayama
Journal:  Chem Pharm Bull (Tokyo)       Date:  2004-08       Impact factor: 1.645
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  17 in total

1.  Scalable total syntheses of N-linked tryptamine dimers by direct indole-aniline coupling: psychotrimine and kapakahines B and F.

Authors:  Timothy Newhouse; Chad A Lewis; Kyle J Eastman; Phil S Baran
Journal:  J Am Chem Soc       Date:  2010-05-26       Impact factor: 15.419

2.  Computational Study on the Conformations of Mitragynine and Mitragynaline.

Authors:  Haining Liu; Christopher R McCurdy; Robert J Doerksen
Journal:  Theochem       Date:  2010-04-15

3.  Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors:  Liangbing Fu; Huw M L Davies
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

4.  General approach to the total synthesis of 9-methoxy-substituted indole alkaloids: synthesis of mitragynine, as well as 9-methoxygeissoschizol and 9-methoxy-N(b)-methylgeissoschizol.

Authors:  Jun Ma; Wenyuan Yin; Hao Zhou; Xuebin Liao; James M Cook
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

5.  Study of the cis to trans isomerization of 1-phenyl-2,3-disubstituted tetrahydro-beta-carbolines at C(1). Evidence for the carbocation-mediated mechanism.

Authors:  Hephzibah J Kumpaty; Michael L Van Linn; M Shahjahan Kabir; F Holger Försterling; Jeffrey R Deschamps; James M Cook
Journal:  J Org Chem       Date:  2009-04-03       Impact factor: 4.354

6.  A chemical synthesis of 11-methoxy mitragynine pseudoindoxyl featuring the interrupted Ugi reaction.

Authors:  Jimin Kim; John S Schneekloth; Erik J Sorensen
Journal:  Chem Sci       Date:  2012-09-01       Impact factor: 9.825

7.  Guanidine alkaloids and Pictet-Spengler adducts from black cohosh (Cimicifuga racemosa).

Authors:  Tanja Gödecke; David C Lankin; Dejan Nikolic; Shao-Nong Chen; Richard B van Breemen; Norman R Farnsworth; Guido F Pauli
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

8.  Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P-(+)-dispegatrine and six other monomeric indole alkaloids.

Authors:  Chitra R Edwankar; Rahul V Edwankar; Ojas A Namjoshi; Xuebin Liao; James M Cook
Journal:  J Org Chem       Date:  2013-06-18       Impact factor: 4.354

Review 9.  Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.

Authors:  Soumen Chakraborty; Susruta Majumdar
Journal:  Biochemistry       Date:  2020-09-22       Impact factor: 3.162

10.  Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles.

Authors:  Pavol Jakubec; Dane M Cockfield; Madeleine Helliwell; James Raftery; Darren J Dixon
Journal:  Beilstein J Org Chem       Date:  2012-04-16       Impact factor: 2.883
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