Literature DB >> 24000234

Enantioselective total synthesis of (-)-minovincine in nine chemical steps: an approach to ketone activation in cascade catalysis.

Brian N Laforteza1, Mark Pickworth, David W C Macmillan.   

Abstract

Dressed to the nines: The first enantioselective total synthesis of (-)-minovincine has been accomplished in nine chemical steps and 13 % overall yield. A novel, one-step Diels-Alder/β-elimination/conjugate addition organocascade sequence allowed rapid access to the central tetracyclic core in an asymmetric manner. Boc=tert-butoxycarbonyl, LG=leaving group, PMB=para-methoxybenzyl.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; enantioselectivity; natural products; organocatalysis; total synthesis

Mesh：

Substances：

Year:  2013        PMID： 24000234      PMCID： PMC3934209          DOI： 10.1002/anie.201305171

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


  11 in total

1.  Direct and enantioselective {alpha}-allylation of ketones via singly occupied molecular orbital (SOMO) catalysis.

Authors:  Anthony Mastracchio; Alexander A Warkentin; Abbas M Walji; David W C MacMillan
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-04       Impact factor: 11.205

Review 2.  Asymmetric organocatalytic domino reactions.

Authors:  Dieter Enders; Christoph Grondal; Matthias R M Hüttl
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Organocascade reactions of enones catalyzed by a chiral primary amine.

Authors:  Li-Yuan Wu; Giorgio Bencivenni; Michele Mancinelli; Andrea Mazzanti; Giuseppe Bartoli; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  The alkaloids of Tabernaemontana riedelii and T. rigida.

Authors:  M P Cava; S S Tjoa; Q A Ahmed; A I Da Rocha
Journal:  J Org Chem       Date:  1968-03       Impact factor: 4.354

5.  First Enantioselective Catalytic Diels-Alder Reaction of Dienes and Acetylenic Aldehydes: Experimental and Theoretical Evidence for the Predominance of Exo-Transition Structure.

Authors:  Kazuaki Ishihara; Shoichi Kondo; Hideki Kurihara; Hisashi Yamamoto; Shigenori Ohashi; Satoshi Inagaki
Journal:  J Org Chem       Date:  1997-05-16       Impact factor: 4.354

6.  The first general enantioselective catalytic Diels-Alder reaction with simple alpha,beta-unsaturated ketones.

Authors:  Alan B Northrup; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2002-03-20       Impact factor: 15.419

7.  Synthesis, thermal stability and resistance to enzymatic hydrolysis of the oligonucleotides containing 5-(N-aminohexyl)carbamoyl-2'-O-methyluridines.

Authors:  Takanori Ito; Yoshihito Ueno; Yasuo Komatsu; Akira Matsuda
Journal:  Nucleic Acids Res       Date:  2003-05-15       Impact factor: 16.971

8.  Regioselective nucleophilic addition to pyridinium salts: a new route to substituted dihydropyridones.

Authors:  Timothy J Donohoe; Matthew J Connolly; Lesley Walton
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

Review 9.  The Catharanthus alkaloids: pharmacognosy and biotechnology.

Authors:  Robert van Der Heijden; Denise I Jacobs; Wim Snoeijer; Didier Hallard; Robert Verpoorte
Journal:  Curr Med Chem       Date:  2004-03       Impact factor: 4.530

10.  Nine-step enantioselective total synthesis of (+)-minfiensine.

Authors:  Spencer B Jones; Bryon Simmons; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419
View more
  6 in total

1.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

2.  Enantioselective construction of cis-hydroindole scaffolds via an asymmetric inverse-electron-demand Diels-Alder reaction: application to the formal total synthesis of (+)-minovincine.

Authors:  Fangqing Zhang; Bing-Tao Ren; Yuqiao Zhou; Yangbin Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2022-04-15       Impact factor: 9.969

3.  Dihydroquinazolinones as adaptative C(sp3) handles in arylations and alkylations via dual catalytic C-C bond-functionalization.

Authors:  Xin-Yang Lv; Roman Abrams; Ruben Martin
Journal:  Nat Commun       Date:  2022-05-03       Impact factor: 17.694

4.  Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

Authors:  Sadhan Jana; Ajay Verma; Rahul Kadu; Sangit Kumar
Journal:  Chem Sci       Date:  2017-07-10       Impact factor: 9.825

5.  Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization.

Authors:  Kang Du; He Yang; Pan Guo; Liang Feng; Guangqing Xu; Qinghai Zhou; Lung Wa Chung; Wenjun Tang
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825

6.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.