Literature DB >> 22280070

Total synthesis of (+)-scholarisine A.

Gregory L Adams1, Patrick J Carroll, Amos B Smith.   

Abstract

An effective total synthesis and assignment of the absolute configuration of the architecturally challenging compound (+)-scholarisine A has been achieved via a 20-step sequence. Highlights include a reductive cyclization involving a nitrile and an epoxide, a modified Fischer indole protocol, a late-stage oxidative lactonization, and an intramolecular cyclization leading to the indolenine ring system of (+)-scholarisine A.
© 2012 American Chemical Society

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Year:  2012        PMID： 22280070      PMCID： PMC3296875          DOI： 10.1021/ja211840k

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


  12 in total

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Authors:  E WENKERT; B WICKBERG
Journal:  J Am Chem Soc       Date:  1965-04-05       Impact factor: 15.419

2.  A cage-monoterpene indole alkaloid from Alstonia scholaris.

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Journal:  Org Lett       Date:  2008-01-19       Impact factor: 6.005

3.  Model studies of the synthesis of echitamine and related indole alkaloids. II.

Authors:  L J Dolby; S J Nelson
Journal:  J Org Chem       Date:  1973-08-10       Impact factor: 4.354

4.  The alkaloid of the leaves of Alstonia scholaris R. Br.

Authors:  A Chatterjee; B Mukherjee; A B Ray; B Das
Journal:  Tetrahedron Lett       Date:  1965-10       Impact factor: 2.415

5.  Model studies of the synthesis of echitamine and related indole alkaloids.

Authors:  L J Dolby; Z Esfandiari
Journal:  J Org Chem       Date:  1972-01-14       Impact factor: 4.354

6.  Alkaloid studies. 53. The structures of nine new alkaloids from Aspidosperma dasycarpon A. DC.

Authors:  J A Joule; M Ohashi; B Gilbert; C Djerassi
Journal:  Tetrahedron       Date:  1965-07       Impact factor: 2.457

7.  Synthesis of the enantiomers of lasiol, an acyclic monoterpene alcohol in the mandibular gland secretion of the male ants, Lasius meridionalis.

Authors:  T Kasai; H Watanabe; K Mori
Journal:  Bioorg Med Chem       Date:  1993-07       Impact factor: 3.641

Review 8.  Current progress in the chemistry and pharmacology of akuammiline alkaloids.

Authors:  Antonio Ramírez; Silvina García-Rubio
Journal:  Curr Med Chem       Date:  2003-09       Impact factor: 4.530

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Authors:  Wei Meng; Bruce A Ellsworth; Alexandra A Nirschl; Peggy J McCann; Manorama Patel; Ravindar N Girotra; Gang Wu; Philip M Sher; Eamonn P Morrison; Scott A Biller; Robert Zahler; Prashant P Deshpande; Annie Pullockaran; Deborah L Hagan; Nathan Morgan; Joseph R Taylor; Mary T Obermeier; William G Humphreys; Ashish Khanna; Lorell Discenza; James G Robertson; Aiying Wang; Songping Han; John R Wetterau; Evan B Janovitz; Oliver P Flint; Jean M Whaley; William N Washburn
Journal:  J Med Chem       Date:  2008-02-09       Impact factor: 7.446

10.  Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia.

Authors:  G Subramaniam; Osamu Hiraku; Masahiko Hayashi; Takashi Koyano; Kanki Komiyama; Toh-Seok Kam
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  10 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

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2.  Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.

Authors:  Jesus Moreno; Elias Picazo; Lucas A Morrill; Joel M Smith; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-01-19       Impact factor: 15.419

3.  Total Synthesis of (+)-Arborisidine.

Authors:  Zhiyao Zhou; Alison X Gao; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2019-05-02       Impact factor: 15.419

Review 4.  Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.

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5.  Pardon the Interruption: A Modification of Fischer's Venerable Reaction for the Synthesis of Heterocycles and Natural Products.

Authors:  Robert B Susick; Lucas A Morrill; Elias Picazo; Neil K Garg
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6.  Access to the akuammiline family of alkaloids: total synthesis of (+)-scholarisine A.

Authors:  Gregory L Adams; Patrick J Carroll; Amos B Smith
Journal:  J Am Chem Soc       Date:  2012-12-26       Impact factor: 15.419

7.  Understanding and Interrupting the Fischer Azaindolization Reaction.

Authors:  Bryan J Simmons; Marie Hoffmann; Pier Alexandre Champagne; Elias Picazo; Katsuya Yamakawa; Lucas A Morrill; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2017-10-12       Impact factor: 15.419

Review 8.  The role of biocatalysis in the asymmetric synthesis of alkaloids.

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Journal:  RSC Adv       Date:  2013-08-07       Impact factor: 3.361

9.  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

10.  Total synthesis of the akuammiline alkaloid picrinine.

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Journal:  J Am Chem Soc       Date:  2014-03-12       Impact factor: 15.419
  10 in total

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