Literature DB >> 28872739

Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.

Beau P Pritchett1, Etienne J Donckele1, Brian M Stoltz1.   

Abstract

Enantioselective Pd-catalyzed allylic alkylations of dihydropyrido[1,2-a]indolone (DHPI) substrates were used to construct the C20-quaternary stereocenters of multiple monoterpene indole alkaloids. Stereodivergent Pictet-Spengler and Bischler-Napieralski cyclization/reduction cascades furnish the cis- and trans-fused azadecalin subunits present in Aspidosperma and Kopsia alkaloids, respectively, en route to highly efficient syntheses of (+)-limaspermidine and (+)-kopsihainanine A.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic alkylation; asymmetric catalysis; monoterpene indole alkaloids; stereodivergent cyclizations; total synthesis

Mesh：

Substances：

Year:  2017        PMID： 28872739      PMCID： PMC5896324          DOI： 10.1002/anie.201707304

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  26 in total

1.  Total synthesis of (±)-kopsihainanine A.

Authors:  Peng Jing; Zhen Yang; Changgui Zhao; Huaiji Zheng; Bowen Fang; Xingang Xie; Xuegong She
Journal:  Chemistry       Date:  2012-04-30       Impact factor: 5.236

2.  Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex.

Authors:  Marc Liniger; David G VanderVelde; Michael K Takase; Mona Shahgholi; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2016-01-12       Impact factor: 15.419

Review 3.  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

4.  Unified strategy to monoterpene indole alkaloids: total syntheses of (±)-goniomitine, (±)-1,2-dehydroaspidospermidine, (±)-aspidospermidine, (±)-vincadifformine, and (±)-kopsihainanine A.

Authors:  Olivier Wagnières; Zhengren Xu; Qian Wang; Jieping Zhu
Journal:  J Am Chem Soc       Date:  2014-10-13       Impact factor: 15.419

5.  Total synthesis of the indole alkaloid (±)- and (+)-methyl N-decarbomethoxychanofruticosinate.

Authors:  Yi Wei; Duo Zhao; Dawei Ma
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-20       Impact factor: 15.336

6.  Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate.

Authors:  Kousuke Tani; Brian M Stoltz
Journal:  Nature       Date:  2006-06-08       Impact factor: 49.962

7.  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

8.  Asymmetric total synthesis of Apocynaceae hydrocarbazole alkaloids (+)-deethylibophyllidine and (+)-limaspermidine.

Authors:  Ji-Yuan Du; Chao Zeng; Xiao-Jie Han; Hu Qu; Xian-He Zhao; Xian-Tao An; Chun-An Fan
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

9.  Formal Synthesis of (+)-Kopsihainanine A and Synthetic Study toward (+)-Limaspermidine.

Authors:  Zhuang Chen; Shiqiang Zhou; Yanxing Jia
Journal:  J Org Chem       Date:  2015-12-07       Impact factor: 4.354

10.  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
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  9 in total

Review 1.  Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

Authors:  Beau P Pritchett; Brian M Stoltz
Journal:  Nat Prod Rep       Date:  2018-06-20       Impact factor: 13.423

2.  Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

Authors:  Hongze Li; Shou-Jie Shen; Cheng-Liang Zhu; Hao Xu
Journal:  J Am Chem Soc       Date:  2019-05-30       Impact factor: 15.419

3.  Short Enantioselective Formal Synthesis of (-)-Platencin.

Authors:  Christian Defieber; Justin T Mohr; Gennadii A Grabovyi; Brian M Stoltz
Journal:  Synthesis (Stuttg)       Date:  2018-07-23       Impact factor: 3.157

Review 4.  Acyclic Twisted Amides.

Authors:  Guangrong Meng; Jin Zhang; Michal Szostak
Journal:  Chem Rev       Date:  2021-08-18       Impact factor: 72.087

5.  Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.

Authors:  Kristen M Flynn; In-Soo Myeong; Taylor Pinto; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2022-05-11       Impact factor: 16.383

6.  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

7.  Palladium-catalyzed tandem allylic substitution/cyclization and cascade hydrosilylated reduction: the influence of reaction parameters and hydrosilanes on the stereoselectivity.

Authors:  Peng-Wei Long; Jian-Xing Xu; Xing-Feng Bai; Zheng Xu; Zhan-Jiang Zheng; Ke-Fang Yang; Li Li; Li-Wen Xu
Journal:  RSC Adv       Date:  2018-06-22       Impact factor: 3.361

8.  The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16'-epi-Leucophyllidine.

Authors:  Christopher E Reimann; Aurapat Ngamnithiporn; Kohei Hayashida; Daisuke Saito; Katerina M Korch; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-06       Impact factor: 16.823

9.  D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation.

Authors:  Michael R Imrich; Jochen Kraft; Cäcilia Maichle-Mössmer; Thomas Ziegler
Journal:  Beilstein J Org Chem       Date:  2018-08-08       Impact factor: 2.883
  9 in total

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