Literature DB >> 29863356

Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.

Alyssa H Antropow1, Nicholas R Garcia1, Kolby L White1, Mohammad Movassaghi1.   

Abstract

The first enantioselective total synthesis of (-)-vallesine via a strategy that features a late-stage regioselective C17-oxidation followed by a highly stereoselective transannular cyclization is reported. The versatility of this approach is highlighted by the divergent synthesis of the archetypal alkaloid of this family, (+)-aspidospermidine, and an A-ring-oxygenated derivative, (+)-deacetylaspidospermine, the precursor to (-)-vallesine, from a common intermediate.

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Year:  2018        PMID： 29863356      PMCID： PMC6021010          DOI： 10.1021/acs.orglett.8b01428

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


  34 in total

1.  Total synthesis of aspidospermine.

Authors:  Y Ban; Y Sato; I Inoue; M Nagai; T Oishi; M Terashima; O Yonemitsu; Y Kanaoka
Journal:  Tetrahedron Lett       Date:  1965-07       Impact factor: 2.415

2.  Pseudoephenamine: a practical chiral auxiliary for asymmetric synthesis.

Authors:  Marvin R Morales; Kevin T Mellem; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-27       Impact factor: 15.336

3.  Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

Authors:  Kolby L White; Marius Mewald; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2015-07-22       Impact factor: 4.354

4.  Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine.

Authors:  James P Lajiness; Wanlong Jiang; Dale L Boger
Journal:  Org Lett       Date:  2012-04-05       Impact factor: 6.005

5.  Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products.

Authors:  Nengzhong Wang; Shuo Du; Dong Li; Xuefeng Jiang
Journal:  Org Lett       Date:  2017-06-01       Impact factor: 6.005

6.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

7.  Boc groups as protectors and directors for Ir-catalyzed C-H borylation of heterocycles.

Authors:  Venkata A Kallepalli; Feng Shi; Sulagna Paul; Edith N Onyeozili; Robert E Maleczka; Milton R Smith
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

8.  Total synthesis of indole and dihydroindole alkaloids. V. The total synthesis of dl-quebrachamine and dl-aspidospermidine. A general entry into the aspidosperma alkaloids.

Authors:  J P Kutney; N Abdurahman; C Gletsos; P Le Quesne; E Piers; I Vlattas
Journal:  J Am Chem Soc       Date:  1970-03-25       Impact factor: 15.419

9.  Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate.

Authors:  Kazuma Amaike; Richard P Loach; Mohammad Movassaghi
Journal:  Organic Synth       Date:  2015

10.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354
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  1 in total

1.  Total Synthesis of (-)-Kopsifoline A and (+)-Kopsifoline E.

Authors:  In-Soo Myeong; Nadide Hazal Avci; Mohammad Movassaghi
Journal:  Org Lett       Date:  2021-11-12       Impact factor: 6.072
  1 in total

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