Literature DB >> 14759191

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

Jianming Yu1, Xiangyu Z Wearing, James M Cook.   

Abstract

The first total syntheses of (-)-vincamajinine (5) (from Na-methyl-d-tryptophan methyl ester) and (-)-11-methoxy-17-epivincamajine (6) (from Na-methyl-6-methoxy-d-tryptophan ethyl ester) are described. The syntheses have been completed in a highly stereocontrolled manner (>98% ee). Key steps included the asymmetric Pictet-Spengler reaction, enolate-mediated palladium cross-coupling reaction, and acid-catalyzed formation of the C(7)-C(17) bond. In addition, the triethylsilane/TFA-mediated incorporation of the 2alpha-H (11 to 12) and the borohydride generation of the C(17) hydroxyl function (R) were also stereospecific. The unique highly conjested carbon skeletons of the two alkaloids were completed in a concise manner and in regiospecific fashion.

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Year:  2004        PMID： 14759191     DOI： 10.1021/ja039798n

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

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

Authors:  Jun Ma; Wenyuan Yin; Hao Zhou; James M Cook
Journal:  Org Lett       Date:  2007-08-08       Impact factor: 6.005

2.  Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

Authors:  Michael Rajesh Stephen; M Toufiqur Rahman; V V N Phani Babu Tiruveedhula; German O Fonseca; Jeffrey R Deschamps; James M Cook
Journal:  Chemistry       Date:  2017-10-18       Impact factor: 5.236

3.  Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A.

Authors:  Wenyuan Yin; M Shahjahan Kabir; Zhijian Wang; Sundari K Rallapalli; Jun Ma; James M Cook
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

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

Review 6.  Sarpagine and Related Alkaloids.

Authors:  Ojas A Namjoshi; James M Cook
Journal:  Alkaloids Chem Biol       Date:  2015-10-09

7.  Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids.

Authors:  Wen Chen; Yonghui Ma; Wenyan He; Yinxia Wu; Yuancheng Huang; Yipeng Zhang; Hongchang Tian; Kai Wei; Xiaodong Yang; Hongbin Zhang
Journal:  Nat Commun       Date:  2022-02-17       Impact factor: 17.694

8.  Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.

Authors:  Elias Picazo; Lucas A Morrill; Robert B Susick; Jesus Moreno; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2018-05-15       Impact factor: 15.419
  8 in total

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