Literature DB >> 16048327

The first regiospecific, enantiospecific total synthesis of 6-oxoalstophylline and an improved total synthesis of alstonerine and alstophylline as well as the bisindole alkaloid macralstonine.

Xuebin Liao1, Hao Zhou, Xiangyu Z Wearing, Jun Ma, James M Cook.   

Abstract

A Wacker sequence has been modified to rapidly generate ring E of (-)-alstonerine, (+)-6-oxoalstophylline, and (-)-alstophylline via a domino process. This one-pot sequence provides facile entry into the dihydropyranyl enone unit of many Alstonia alkaloids. [structure: see text]

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Year:  2005        PMID： 16048327     DOI： 10.1021/ol051208y

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


  11 in total

1.  Concise, enantioselective total synthesis of (-)-alstonerine.

Authors:  Kenneth A Miller; Stephen F Martin
Journal:  Org Lett       Date:  2007-02-14       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.  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.  A two step synthesis of BzR/GABAergic active flavones via a Wacker-related oxidation.

Authors:  Michael Lorenz; M Shahjahan Kabir; James M Cook
Journal:  Tetrahedron Lett       Date:  2010-02-17       Impact factor: 2.415

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.  The Pauson-Khand Reaction as a New Entry to the Synthesis of Bridged Bicyclic Heterocycles: Application to the Enantioselective Total Synthesis of (-)-Alstonerine.

Authors:  Kenneth A Miller; Charles S Shanahan; Stephen F Martin
Journal:  Tetrahedron       Date:  2008       Impact factor: 2.457

Review 7.  Sarpagine and Related Alkaloids.

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

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

Review 9.  Bisindole Alkaloids from the Alstonia Species: Recent Isolation, Bioactivity, Biosynthesis, and Synthesis.

Authors:  Kamal P Pandey; Md Toufiqur Rahman; James M Cook
Journal:  Molecules       Date:  2021-06-07       Impact factor: 4.411

10.  Stereospecific total synthesis of the indole alkaloid ervincidine. Establishment of the C-6 hydroxyl stereochemistry.

Authors:  Sundari K Rallapalli; Ojas A Namjoshi; V V N Phani Babu Tiruveedhula; Jeffrey R Deschamps; James M Cook
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354
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