Literature DB >> 16608311

Enantioselective total synthesis of bistramide A.

Michael T Crimmins1, Amy C DeBaillie.   

Abstract

The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments.

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Year:  2006        PMID： 16608311      PMCID： PMC2546575          DOI： 10.1021/ja057686l

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


  13 in total

1.  Systematic assignment of the configuration of flexible natural products by spectroscopic and computational methods: the bistramide C analysis.

Authors:  Gérard Zuber; Michael-Rock Goldsmith; Tamara D Hopkins; David N Beratan; Peter Wipf
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

2.  Total synthesis and structure validation of (+)-bistramide C.

Authors:  Peter Wipf; Tamara D Hopkins
Journal:  Chem Commun (Camb)       Date:  2005-06-01       Impact factor: 6.222

3.  Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones.

Authors:  M T Crimmins; B W King; E A Tabet; K Chaudhary
Journal:  J Org Chem       Date:  2001-02-09       Impact factor: 4.354

4.  Blockade of sodium channels by Bistramide A in voltage-clamped frog skeletal muscle fibres.

Authors:  M P Sauviat; D Gouiffes-Barbin; E Ecault; J F Verbist
Journal:  Biochim Biophys Acta       Date:  1992-01-10

5.  Stimulation of protein kinase C-dependent and -independent signaling pathways by bistratene A in intestinal epithelial cells.

Authors:  M R Frey; O Leontieva; D J Watters; J D Black
Journal:  Biochem Pharmacol       Date:  2001-05-01       Impact factor: 5.858

6.  Synthesis and [4 + 2]-annulation of enantioenriched (z)-crotylsilanes: preparation of the C1-C13 fragment of bistramide A.

Authors:  Jason T Lowe; James S Panek
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

7.  Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the Evans asymmetric alkylation.

Authors:  M T Crimmins; K A Emmitte; J D Katz
Journal:  Org Lett       Date:  2000-07-13       Impact factor: 6.005

8.  Improved procedure for the reductive acetylation of acyclic esters and a new synthesis of ethers.

Authors:  D J Kopecky; S D Rychnovsky
Journal:  J Org Chem       Date:  2000-01-14       Impact factor: 4.354

9.  Bistramides A, B, C, D, and K: a new class of bioactive cyclic polyethers from Lissoclinum bistratum.

Authors:  J F Biard; C Roussakis; J M Kornprobst; D Gouiffes-Barbin; J F Verbist; P Cotelle; M P Foster; C M Ireland; C Debitus
Journal:  J Nat Prod       Date:  1994-10       Impact factor: 4.050

10.  Novel cytotoxic compounds from the ascidian Lissoclinum bistratum.

Authors:  B M Degnan; C J Hawkins; M F Lavin; E J McCaffrey; D L Parry; D J Watters
Journal:  J Med Chem       Date:  1989-06       Impact factor: 7.446
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  10 in total

1.  INTEGRATED APPROACHES TO THE CONFIGURATIONAL ASSIGNMENT OF MARINE NATURAL PRODUCTS.

Authors:  Tadeusz F Molinski; Brandon I Morinaka
Journal:  Tetrahedron       Date:  2012-11-18       Impact factor: 2.457

2.  Enantioselective total synthesis and structural assignment of callyspongiolide.

Authors:  Arun K Ghosh; Luke A Kassekert; Joseph D Bungard
Journal:  Org Biomol Chem       Date:  2016-12-07       Impact factor: 3.876

3.  Iridium Catalysts for Acceptorless Dehydrogenation of Alcohols to Carboxylic Acids: Scope and Mechanism.

Authors:  Valeriy Cherepakhin; Travis J Williams
Journal:  ACS Catal       Date:  2018-03-26       Impact factor: 13.084

4.  Enantioselective Synthesis of Both Epimers at C-21 in the Proposed Structure of Cytotoxic Macrolide Callyspongiolide.

Authors:  Arun K Ghosh; Luke A Kassekert
Journal:  Org Lett       Date:  2016-06-22       Impact factor: 6.005

5.  One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes.

Authors:  Vladimir A Maslivetc; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2015-08-05       Impact factor: 3.876

6.  Spiroacetal formation through telescoped cycloaddition and carbon-hydrogen bond functionalization: total synthesis of bistramide A.

Authors:  Xun Han; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

7.  Synthesis of a 35-member stereoisomer library of bistramide A: evaluation of effects on actin state, cell cycle and tumor cell growth.

Authors:  Iwona E Wrona; Jason T Lowe; Thomas J Turbyville; Tanya R Johnson; Julien Beignet; John A Beutler; James S Panek
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

Review 8.  Asymmetric synthesis of naturally occurring spiroketals.

Authors:  B Rama Raju; Anil K Saikia
Journal:  Molecules       Date:  2008-08-28       Impact factor: 4.411

9.  A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants.

Authors:  Yong Chen; Guilhem Coussanes; Caroline Souris; Paul Aillard; Dainis Kaldre; Kathrin Runggatscher; Stefan Kubicek; Giovanni Di Mauro; Boris Maryasin; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2019-08-22       Impact factor: 16.383

10.  The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry.

Authors:  Justine N deGruyter; William A Maio
Journal:  Org Lett       Date:  2014-09-23       Impact factor: 6.005
  10 in total

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