Literature DB >> 20795730

Total synthesis of rhazinilam: axial to point chirality transfer in an enantiospecific Pd-catalyzed transannular cyclization.

Zhenhua Gu1, Armen Zakarian.   

Abstract

A total synthesis of rhazinilam based on a transannular cyclization strategy is described. Using a Heck reaction, the axial chirality of a halogenated 13-membered lactam can be exploited to create the quaternary chiral stereogenic center in the target molecule with high enantiospecificity.

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Year:  2010        PMID： 20795730      PMCID： PMC3071635          DOI： 10.1021/ol101523z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  19 in total

1.  Total synthesis of (-)-rhazinilam: asymmetric C[bond]H bond activation via the use of a chiral auxiliary.

Authors:  James A Johnson; Ning Li; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

2.  Total synthesis of (+/-)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi.

Authors:  Martin G Banwell; Alison J Edwards; Katrina A Jolliffe; Jason A Smith; Ernest Hamel; Pascal Verdier-Pinard
Journal:  Org Biomol Chem       Date:  2003-01-21       Impact factor: 3.876

3.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  Activation of macrocyclic enediynes by transannular cyclization.

Authors:  Amit Basak; Sandip Kumar Roy; Subrata Mandal
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-17       Impact factor: 15.336

5.  Au(I)-catalyzed annulation of enantioenriched allenes in the enantioselective total synthesis of (-)-rhazinilam.

Authors:  Zuosheng Liu; Andrew S Wasmuth; Scott G Nelson
Journal:  J Am Chem Soc       Date:  2006-08-16       Impact factor: 15.419

6.  Total Synthesis of (+)-Gelsedine.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

7.  Catalytic, asymmetric transannular aldolizations: total synthesis of (+)-hirsutene.

Authors:  Carley L Chandler; Benjamin List
Journal:  J Am Chem Soc       Date:  2008-05-03       Impact factor: 15.419

8.  Memory of chirality in the transannular cyclization of cyclodecenyl radicals.

Authors:  Jackline E Dalgard; Scott D Rychnovsky
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

9.  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

10.  Synthesis of pyrrolnitrin and related halogenated phenylpyrroles.

Authors:  Matthew D Morrison; Jason J Hanthorn; Derek A Pratt
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005
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  9 in total

1.  Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group.

Authors:  Enver Cagri Izgu; Thomas R Hoye
Journal:  Chem Sci       Date:  2013-02       Impact factor: 9.825

2.  Total Synthesis of Hyacinthacine A2: Stereocontrolled 5-aza-cyclooctene Photoisomerization and Transannular Hydroamination with Planar-to-Point Chirality Transfer.

Authors:  Maksim Royzen; Michael T Taylor; Andrew Deangelis; Joseph M Fox
Journal:  Chem Sci       Date:  2011-11       Impact factor: 9.825

3.  A Model Study toward the Concise Synthesis of Bromotyrosine Derived Spiroisoxazoline Natural Products and Analogous Core Structures.

Authors:  Prasanta Das; Edward J Valente; Ashton T Hamme
Journal:  European J Org Chem       Date:  2014-05-01

4.  Formal total syntheses of classic natural product target molecules via palladium-catalyzed enantioselective alkylation.

Authors:  Yiyang Liu; Marc Liniger; Ryan M McFadden; Jenny L Roizen; Jacquie Malette; Corey M Reeves; Douglas C Behenna; Masaki Seto; Jimin Kim; Justin T Mohr; Scott C Virgil; Brian M Stoltz
Journal:  Beilstein J Org Chem       Date:  2014-10-28       Impact factor: 2.883

5.  Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions†Electronic supplementary information (ESI) available: Experimental details and procedures, compound characterization data, copies of 1H and 13C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file.

Authors:  Zining Li; Qian Geng; Zhe Lv; Beau P Pritchett; Katsuaki Baba; Yoshitaka Numajiri; Brian M Stoltz; Guangxin Liang
Journal:  Org Chem Front       Date:  2015-01-27       Impact factor: 5.281

6.  Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.

Authors:  Yang Yang; Yu Bai; Siyuan Sun; Mingji Dai
Journal:  Org Lett       Date:  2014-11-20       Impact factor: 6.005

Review 7.  Medicinal Plants from Near East for Cancer Therapy.

Authors:  Mohammad S Abu-Darwish; Thomas Efferth
Journal:  Front Pharmacol       Date:  2018-01-31       Impact factor: 5.810

8.  Programmed serial stereochemical relay and its application in the synthesis of morphinans.

Authors:  Kun Ho Kenny Park; Rui Chen; David Y-K Chen
Journal:  Chem Sci       Date:  2017-08-30       Impact factor: 9.825

9.  Gene Expression Profiling to Delineate the Anticancer Potential of a New Alkaloid Isopicrinine From Rhazya stricta.

Authors:  Nahid H Hajrah; Waseem Mohammed Abdul; Zainab H Abdul-Hameed; Walied M Alarif; Nouf Saeed A Al-Abbas; Seif-Eldin N Ayyad; Abdulkader M Shaikh Omer; Mohammed Zainy Mutawakil; Neil Hall; Abdullah Y Obaid; Roop Singh Bora; Jamal S M Sabir; Kulvinder Singh Saini
Journal:  Integr Cancer Ther       Date:  2020 Jan-Dec       Impact factor: 3.279
  9 in total

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