Literature DB >> 16819859

Efficient synthetic access to the hetisine C20-diterpenoid alkaloids. A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions.

Kevin M Peese1, David Y Gin.   

Abstract

A concise synthetic approach to the hetisine C20-diterpenoid alkaloids is reported. The total synthesis of (+/-)-nominine was accomplished in a 15-step sequence employing a dual cycloaddition strategy. Key features of the synthesis include a reversible intramolecular 4-oxidoisoquinolinium betaine dipolar cycloaddition in conjunction with a pyrrolidine-induced dienamine isomerization/Diels-Alder cascade.

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Year:  2006        PMID： 16819859      PMCID： PMC2610465          DOI： 10.1021/ja0625430

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


  10 in total

1.  Facile synthesis of the tricyclic core of sarain A. 3-Oxidopyridinium betaine cycloaddition approach.

Authors:  M J Sung; H I Lee; Y Chong; J K Cha
Journal:  Org Lett       Date:  1999-12-16       Impact factor: 6.005

Review 2.  C20-diterpenoid alkaloids.

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

3.  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

4.  3-Hydroxy-4-pyrones as Precursors of 4-Methoxy-3-oxidopyridinium Ylides. An Expeditious Entry to Highly Substituted 8-Azabicyclo[3.2.1]octanes.

Authors:  Antonio Rumbo; Antonio Mouriño; Luis Castedo; José L. Mascareñas
Journal:  J Org Chem       Date:  1996-09-06       Impact factor: 4.354

5.  Ring-substituted [1,2-bis(4-hydroxyphenyl)ethylenediamine]dichloroplatinum (II) complexes: compounds with a selective effect on the hormone-dependent mammary carcinoma.

Authors:  J Karl; R Gust; T Spruss; M R Schneider; H Schönenberger; J Engel; K H Wrobel; F Lux; S T Haeberlin
Journal:  J Med Chem       Date:  1988-01       Impact factor: 7.446

6.  Synthesis of 6-aza-bicyclo[3,2,1]octan-3-ones via vinylogous imide photochemistry: an approach to the synthesis of the hetisine alkaloids.

Authors:  Y S Kwak; J D Winkler
Journal:  J Am Chem Soc       Date:  2001-08-01       Impact factor: 15.419

7.  Enantioselective approach to the hetisine alkaloids. Synthesis of the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core via intramolecular dipolar cycloaddition.

Authors:  Kevin M Peese; David Y Gin
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

Review 8.  Synthetic applications of heteroaromatic betaines with six-membered rings.

Authors:  N Dennis; A R Katritzky; Y Takeuchi
Journal:  Angew Chem Int Ed Engl       Date:  1976-01       Impact factor: 15.336

9.  Bridgehead arylation: a direct route to advanced intermediates for the synthesis of C-20 diterpene alkaloids.

Authors:  Craig M Williams; Lewis N Mander
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

10.  Synthesis and pharmacology of 8-amino-3-(cyclopropylmethyl)-1,2,3,4,5,6-hexahydro-cis-6,11-dimethyl-2,6-methano-3-benzazocine and related compounds.

Authors:  M P Wentland; N F Albertson; A K Pierson
Journal:  J Med Chem       Date:  1980-01       Impact factor: 7.446
  10 in total
  14 in total

1.  Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

Authors:  Christopher J Huck; David Sarlah
Journal:  Chem       Date:  2020-07-01       Impact factor: 22.804

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

Review 4.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

5.  (4+3) cycloaddition reactions of nitrogen-stabilized oxyallyl cations.

Authors:  Andrew G Lohse; Richard P Hsung
Journal:  Chemistry       Date:  2011-03-07       Impact factor: 5.236

6.  ESIPT-mediated photocycloadditions of 3-hydroxyquinolinones: development of a fluorescence quenching assay for reaction screening.

Authors:  Bing Xia; Baudouin Gerard; Danielle M Solano; Jiandi Wan; Guilford Jones; John A Porco
Journal:  Org Lett       Date:  2011-02-21       Impact factor: 6.005

7.  Terpenoid-Alkaloids: Their Biosynthetic Twist of Fate and Total Synthesis.

Authors:  Emily C Cherney; Phil S Baran
Journal:  Isr J Chem       Date:  2011-04-01       Impact factor: 3.333

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

Authors:  Kevin G M Kou; Beryl X Li; Jack C Lee; Gary M Gallego; Terry P Lebold; Antonio G DiPasquale; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2016-08-22       Impact factor: 15.419

9.  Gallium(III)-catalyzed cycloisomerization approach to the diterpenoid alkaloids: construction of the core structure for the hetidines and hetisines.

Authors:  Amy M Hamlin; Felipe de Jesus Cortez; David Lapointe; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-26       Impact factor: 15.336

10.  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
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