Literature DB >> 11101452

Studies directed toward the total synthesis of azaspiracid: stereoselective construction of C(1)-C(12), C(13)-C(19), and C(21)-C(25) fragments.

R G Carter1, D J Weldon.   

Abstract

[reaction: see text] The efficient entry to the C(1)-C(12), C(13)-C(19), and C(21)-C(25) fragments of azaspiracid is outlined. The C(1)-C(12) portion is constructed using a key asymmetric allenyl borane addition to the corresponding alpha,beta-unsaturated aldehyde. The synthesis of the C(13)-C(19) portion utilizes an Evans asymmetric alkylation followed by Sharpless asymmetric dihydroxylation. In addition, a novel solution to the mismatched effects of a neighboring chiral oxazolidinone during a Sharpless dihydroxylation is detailed.

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Year:  2000        PMID： 11101452     DOI： 10.1021/ol006674w

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


  11 in total

1.  Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1.

Authors:  Xiao-Ti Zhou; Rich G Carter
Journal:  Chem Commun (Camb)       Date:  2004-09-20       Impact factor: 6.222

2.  Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization.

Authors:  Xiao-Ti Zhou; Liang Lu; Daniel P Furkert; Charles E Wells; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

3.  Synthesis of the C1-C26 northern portion of azaspiracid-1: kinetic versus thermodynamic control of the formation of the bis-spiroketal.

Authors:  Xiao-Ti Zhou; Rich G Carter
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-03       Impact factor: 15.336

4.  Synthetic and Computational Studies on the ABC Trioxadispiroketal Subunit of the Marine Biotoxin Azaspiracid-1.

Authors:  Jialiang Li; Xiaohua Li; David R Mootoo
Journal:  Nat Prod Commun       Date:  2008-11       Impact factor: 0.986

5.  Amphidinolide B: total synthesis, structural investigation, and biological evaluation.

Authors:  Liang Lu; Wei Zhang; Sangkil Nam; David A Horne; Richard Jove; Rich G Carter
Journal:  J Org Chem       Date:  2013-02-13       Impact factor: 4.354

6.  Synthetic studies toward amphidinolide B1: synthesis of the C9-C26 fragment.

Authors:  Wei Zhang; Rich G Carter
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

7.  Synthesis of complex allylic esters via C-H oxidation vs C-C bond formation.

Authors:  Nicolaas A Vermeulen; Jared H Delcamp; M Christina White
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

8.  Synthesis of the ABC ring system of Azaspiracid. 2. A systematic study into the effect of C(16) and C(17) substitution on bis-spirocyclization.

Authors:  Rich G Carter; David E Graves; Melissa A Gronemeyer; Gregory S Tschumper
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

9.  Synthesis of the ABC ring system of azaspiracid. 1. Effect of D ring truncation on bis-spirocyclization.

Authors:  Rich G Carter; T Campbell Bourland; David E Graves
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

10.  Exploiting hidden symmetry in natural products: total syntheses of amphidinolides C and F.

Authors:  Subham Mahapatra; Rich G Carter
Journal:  J Am Chem Soc       Date:  2013-07-11       Impact factor: 15.419
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