Literature DB >> 27525345

Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, N-Ethyl-1α-hydroxy-17-veratroyldictyzine, and Paniculamine.

Kevin G M Kou1, Beryl X Li1, Jack C Lee1, Gary M Gallego1, Terry P Lebold1, Antonio G DiPasquale1, Richmond Sarpong1.   

Abstract

The denudatine-type diterpenoid alkaloids cochlearenine, N-ethyl-1α-hydroxy-17-veratroyldictyzine, and paniculamine have been synthesized for the first time (25, 26, and 26 steps from 16, respectively). These syntheses take advantage of a common intermediate (8) that we have previously employed in preparing aconitine-type natural products. The syntheses reported herein complete the realization of a unified strategy for the preparation of C20, C19, and C18 diterpenoid alkaloids.

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Year:  2016        PMID： 27525345      PMCID： PMC5076861          DOI： 10.1021/jacs.6b07268

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


  32 in total

Review 1.  C20-diterpenoid alkaloids.

Authors:  Feng-Peng Wang; Xiao-Tian Liang
Journal:  Alkaloids Chem Biol       Date:  2002

2.  Total synthesis of (+/-)-nominine, a heptacyclic hetisine-type aconite alkaloid.

Authors:  Hideaki Muratake; Mitsutaka Natsume
Journal:  Angew Chem Int Ed Engl       Date:  2004-09-06       Impact factor: 15.336

3.  The C19-diterpenoid alkaloids.

Authors:  Feng-Peng Wang; Qiao-Hong Chen
Journal:  Alkaloids Chem Biol       Date:  2010

Review 4.  The C18-diterpenoid alkaloids.

Authors:  Feng-Peng Wang; Qiao-Hong Chen; Xiao-Tian Liang
Journal:  Alkaloids Chem Biol       Date:  2009

5.  Total Synthesis of (-)-Cardiopetaline.

Authors:  Yoshitake Nishiyama; Satoshi Yokoshima; Tohru Fukuyama
Journal:  Org Lett       Date:  2016-05-11       Impact factor: 6.005

6.  Pharmacological actions of aconitine alkaloids.

Authors:  H Sato; C Yamada; C Konno; Y Ohizumi; K Endo; H Hikino
Journal:  Tohoku J Exp Med       Date:  1979-06       Impact factor: 1.848

7.  A guide to small-molecule structure assignment through computation of (¹H and ¹³C) NMR chemical shifts.

Authors:  Patrick H Willoughby; Matthew J Jansma; Thomas R Hoye
Journal:  Nat Protoc       Date:  2014-02-20       Impact factor: 13.491

8.  A concise ring-expansion route to the compact core of platensimycin.

Authors:  Nicholas A McGrath; Emily S Bartlett; Satapanawat Sittihan; Jon T Njardarson
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Asymmetric synthetic access to the hetisine alkaloids: total synthesis of (+)-nominine.

Authors:  Kevin M Peese; David Y Gin
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

Review 10.  Bioinspired iterative synthesis of polyketides.

Authors:  Kuan Zheng; Changmin Xie; Ran Hong
Journal:  Front Chem       Date:  2015-05-21       Impact factor: 5.221
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  7 in total

1.  A Copper-Mediated Conjugate Addition Approach to Analogues of Aconitine-Type Diterpenoid Alkaloids.

Authors:  Nicolle A Doering; Kevin G M Kou; Krissada Norseeda; Jack C Lee; Christopher J Marth; Gary M Gallego; Richmond Sarpong
Journal:  J Org Chem       Date:  2018-09-28       Impact factor: 4.354

2.  A Benzyne Insertion Approach to Hetisine-Type Diterpenoid Alkaloids: Synthesis of Cossonidine (Davisine).

Authors:  Kevin G M Kou; Jason J Pflueger; Toshihiro Kiho; Louis C Morrill; Ethan L Fisher; Kyle Clagg; Terry P Lebold; Jessica K Kisunzu; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2018-06-19       Impact factor: 15.419

3.  Magnesiate Addition/Ring-Expansion Strategy To Access the 6-7-6 Tricyclic Core of Hetisine-Type C20-Diterpenoid Alkaloids.

Authors:  Jason J Pflueger; Louis C Morrill; Justine N deGruyter; Melecio A Perea; Richmond Sarpong
Journal:  Org Lett       Date:  2017-08-18       Impact factor: 6.005

4.  Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy Inspired by Chemical Network Analysis.

Authors:  Kyle R Owens; Shelby V McCowen; Katherine A Blackford; Sohei Ueno; Yasuo Hirooka; Manuel Weber; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2019-08-21       Impact factor: 15.419

5.  A Unifying Synthesis Approach to the C18-, C19-, and C20-Diterpenoid Alkaloids.

Authors:  Kevin G M Kou; Svitlana Kulyk; Christopher J Marth; Jack C Lee; Nicolle A Doering; Beryl X Li; Gary M Gallego; Terry P Lebold; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2017-09-20       Impact factor: 15.419

Review 6.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

Review 7.  Recent Advances in Substrate-Controlled Asymmetric Cyclization for Natural Product Synthesis.

Authors:  Jeyun Jo; Seok-Ho Kim; Young Taek Han; Jae-Hwan Kwak; Hwayoung Yun
Journal:  Molecules       Date:  2017-06-26       Impact factor: 4.411
  7 in total

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