Literature DB >> 12431077

A de novo enantioselective total synthesis of (-)-laulimalide.

Scott G Nelson1, Wing S Cheung, Andrew J Kassick, Mark A Hilfiker.   

Abstract

An enantioselective total synthesis of the naturally occurring anticancer agent (-)-laulimalide is described. The synthesis is characterized by extensive use of new reaction methodologies based on catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions and transformations of the derived enantioenriched beta-lactones. The synthesis also incorporates a unique allenylstannane glycal acetate alkylation and chemoselective ring-closing metathesis reaction.

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Year:  2002        PMID： 12431077     DOI： 10.1021/ja028019k

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


  12 in total

1.  Total synthesis of laulimalide: synthesis of the northern and southern fragments.

Authors:  Barry M Trost; W Michael Seganish; Cheol K Chung; Dominique Amans
Journal:  Chemistry       Date:  2012-02-03       Impact factor: 5.236

2.  Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

Authors:  Elsie C Yu; Brett M Johnson; Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

3.  Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations.

Authors:  Shi Chen; Ahmad A Ibrahim; Nicholas J Peraino; Divya Nalla; Mukulesh Mondal; Maxwell Van Raaphorst; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-08-12       Impact factor: 4.354

4.  Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones.

Authors:  Aaron Christopher; Dahniel Brandes; Stephen Kelly; Thomas G Minehan
Journal:  Org Biomol Chem       Date:  2013-10-10       Impact factor: 3.876

5.  Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P.

Authors:  Barry M Trost; Julien P N Papillon; Thomas Nussbaumer
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

6.  Asymmetric synthesis of 2 degrees- and 3 degrees-Carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes.

Authors:  José G Roman; John A Soderquist
Journal:  J Org Chem       Date:  2007-11-14       Impact factor: 4.354

7.  Evaluating transition-metal-catalyzed transformations for the synthesis of laulimalide.

Authors:  Barry M Trost; Dominique Amans; W Michael Seganish; Cheol K Chung
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

8.  Microtubule-stabilizing agents based on designed laulimalide analogues.

Authors:  Susan L Mooberry; Deborah A Randall-Hlubek; Rachel M Leal; Sayee G Hegde; Robert D Hubbard; Lei Zhang; Paul A Wender
Journal:  Proc Natl Acad Sci U S A       Date:  2004-05-25       Impact factor: 11.205

9.  Fragmentation of bicyclic γ-silyloxy-β-hydroxy-α-diazolactones as an approach to ynolides.

Authors:  Ali Bayir; Matthias Brewer
Journal:  J Org Chem       Date:  2014-06-12       Impact factor: 4.354

10.  Preparation of macrocyclic Z-enoates and (E,Z)- or (Z,E)-dienoates through catalytic stereoselective ring-closing metathesis.

Authors:  Hanmo Zhang; Elsie C Yu; Sebastian Torker; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-11-17       Impact factor: 15.419
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