Literature DB >> 29658039

Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

Beau P Pritchett1, Brian M Stoltz.   

Abstract

Covering: up to the end of 2017 Enantioselective Pd-catalyzed allylic alkylations of prochiral enolates represent a powerful tool for the construction of all-carbon quaternary stereocenters. This review describes the emergence of such reactions as strategic linchpins that enable efficient, stereocontrolled syntheses of Aspidosperma and related monoterpene indole alkaloids.

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Year:  2018        PMID： 29658039      PMCID： PMC6013405          DOI： 10.1039/c7np00069c

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN： 0265-0568            Impact factor:   13.423


  58 in total

1.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

Review 2.  Chemistry and biology of monoterpene indole alkaloid biosynthesis.

Authors:  Sarah E O'Connor; Justin J Maresh
Journal:  Nat Prod Rep       Date:  2006-05-26       Impact factor: 13.423

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.  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

5.  Synthesis and Exploration of Electronically Modified (R)-5,5-Dimethyl-(p-CF3)3-i-PrPHOX in Palladium-Catalyzed Enantio- and Diastereoselective Allylic Alkylation: A Practical Alternative to (R)-(p-CF3)3-t-BuPHOX.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2015-08-05       Impact factor: 2.415

6.  Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams.

Authors:  Mercedes Amat; Oscar Lozano; Carmen Escolano; Elies Molins; Joan Bosch
Journal:  J Org Chem       Date:  2007-05-09       Impact factor: 4.354

7.  Rhazinilam and quebrachamine derivatives from Yunnan Kopsia arborea.

Authors:  Yuqiu Wu; Mayu Suehiro; Mariko Kitajima; Takeshi Matsuzaki; Shusuke Hashimoto; Masato Nagaoka; Rongping Zhang; Hiromitsu Takayama
Journal:  J Nat Prod       Date:  2009-02-27       Impact factor: 4.050

8.  Application of a Raney-cobalt-mediated tandem reductive cyclization protocol to total syntheses of the Aspidosperma alkaloids (±)-limaspermidine and (±)-1-acetylaspidoalbidine.

Authors:  Shen H Tan; Martin G Banwell; Anthony C Willis; Tristan A Reekie
Journal:  Org Lett       Date:  2012-10-30       Impact factor: 6.005

9.  Melodinines A-G, monoterpenoid indole alkaloids from Melodinus henryi.

Authors:  Tao Feng; Xiang-Hai Cai; Ya-Ping Liu; Yan Li; Yuan-Yuan Wang; Xiao-Dong Luo
Journal:  J Nat Prod       Date:  2010-01       Impact factor: 4.050

10.  Rhazinilam mimics the cellular effects of taxol by different mechanisms of action.

Authors:  B David; T Sévenet; M Morgat; G Guénard; A Moisand; Y Tollon; O Thoison; M Wright
Journal:  Cell Motil Cytoskeleton       Date:  1994
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  6 in total

1.  Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones.

Authors:  Douglas C Duquette; Alexander Q Cusumano; Louise Lefoulon; Jared T Moore; Brian M Stoltz
Journal:  Org Lett       Date:  2020-06-16       Impact factor: 6.005

2.  Synthesis of 8-Hydroxygeraniol.

Authors:  Francesca M Ippoliti; Joyann S Barber; Yi Tang; Neil K Garg
Journal:  J Org Chem       Date:  2018-07-23       Impact factor: 4.354

3.  Collected mass spectrometry data on monoterpene indole alkaloids from natural product chemistry research.

Authors:  Alexander E Fox Ramos; Pierre Le Pogam; Charlotte Fox Alcover; Elvis Otogo N'Nang; Gaëla Cauchie; Hazrina Hazni; Khalijah Awang; Dimitri Bréard; Antonio M Echavarren; Michel Frédérich; Thomas Gaslonde; Marion Girardot; Raphaël Grougnet; Mariia S Kirillova; Marina Kritsanida; Christelle Lémus; Anne-Marie Le Ray; Guy Lewin; Marc Litaudon; Lengo Mambu; Sylvie Michel; Fedor M Miloserdov; Michael E Muratore; Pascal Richomme-Peniguel; Fanny Roussi; Laurent Evanno; Erwan Poupon; Pierre Champy; Mehdi A Beniddir
Journal:  Sci Data       Date:  2019-04-03       Impact factor: 6.444

4.  A Unified Approach to Polycyclic Alkaloids of the Ingenamine Estate: Total Syntheses of Keramaphidin B, Ingenamine, and Nominal Njaoamine I.

Authors:  Zhanchao Meng; Simon M Spohr; Sandra Tobegen; Christophe Farès; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2021-08-27       Impact factor: 15.419

5.  Total Synthesis Provides Strong Evidence: Xestocyclamine A is the Enantiomer of Ingenamine.

Authors:  Zhanchao Meng; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2020-06-23       Impact factor: 15.419

6.  Synthesis of tetracyclic spiroindolines by an interrupted Bischler-Napieralski reaction: total synthesis of akuammicine.

Authors:  Matteo Faltracco; Eelco Ruijter
Journal:  Org Biomol Chem       Date:  2021-11-18       Impact factor: 3.876
  6 in total

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