Literature DB >> 10891229

General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine.

T Wang1, J M Cook.   

Abstract

[reaction: see text] (+)-Vellosimine has been synthesized enantiospecifically in 27% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled intramolecular palladium-coupling reaction as key steps.

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Year:  2000        PMID： 10891229     DOI： 10.1021/ol000095+

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


  15 in total

1.  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

2.  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

3.  A divergent strategy for the synthesis of secologanin derived natural products.

Authors:  Brandon J English; Robert M Williams
Journal:  J Org Chem       Date:  2010-10-22       Impact factor: 4.354

4.  Brønsted acid mediated cyclization of enaminones. Rapid and efficient access to the tetracyclic framework of the Strychnos alkaloids.

Authors:  Rahul V Edwankar; Chitra R Edwankar; Ojas A Namjoshi; Jeffrey R Deschamps; James M Cook
Journal:  J Nat Prod       Date:  2012-01-18       Impact factor: 4.050

5.  Total Synthesis of Macrocarpines D and E via an Enolate-Driven Copper-Mediated Cross-Coupling Process: Replacement of Catalytic Palladium with Copper Iodide.

Authors:  M Toufiqur Rahman; Jeffrey R Deschamps; Gregory H Imler; Alan W Schwabacher; James M Cook
Journal:  Org Lett       Date:  2016-08-16       Impact factor: 6.005

6.  A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Authors:  Stephen D Holmbo; Nicole A Godfrey; Joshua J Hirner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2016-09-16       Impact factor: 15.419

7.  Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

Authors:  Alan M Hyde; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

8.  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

9.  Total synthesis of the strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclization.

Authors:  Amy B Dounay; Philip G Humphreys; Larry E Overman; Aaron D Wrobleski
Journal:  J Am Chem Soc       Date:  2008-02-28       Impact factor: 15.419

10.  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
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