Literature DB >> 19199776

Studies toward the synthesis of spirolides: assembly of the elaborated E-ring fragment.

Craig E Stivala1, Armen Zakarian.   

Abstract

A stereoselective synthesis of the spiroimine fragment of spirolide C is described. The congested C7 and C29 tertiary and quaternary centers are constructed by a diastereoselective Ireland-Claisen rearrangement. The E ring is completed by means of an aldol cyclocondensation. Additional studies were preformed on the advanced intermediate to probe a future coupling strategy.

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Year:  2009        PMID： 19199776      PMCID： PMC2756537          DOI： 10.1021/ol8027797

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


  16 in total

1.  Characterization of spirolides a, c, and 13-desmethyl c, new marine toxins isolated from toxic plankton and contaminated shellfish.

Authors:  T Hu; I W Burton; A D Cembella; J M Curtis; M A Quilliam; J A Walter; J L Wright
Journal:  J Nat Prod       Date:  2001-03       Impact factor: 4.050

2.  A formal total synthesis of (+)-pinnatoxin A.

Authors:  Satoshi Sakamoto; Hayato Sakazaki; Koji Hagiwara; Kei Kamada; Kento Ishii; Takeshi Noda; Masayuki Inoue; Masahiro Hirama
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-03       Impact factor: 15.336

3.  Stereochemistry of pteriatoxins A, B, and C.

Authors:  Junliang Hao; Fumiyoshi Matsuura; Yoshito Kishi; Masaki Kita; Daisuke Uemura; Naoki Asai; Takashi Iwashita
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

4.  Mechanism of methyl esterification of carboxylic acids by trimethylsilyldiazomethane.

Authors:  Erik Kühnel; David D P Laffan; Guy C Lloyd-Jones; Teresa Martínez Del Campo; Ian R Shepperson; Jennifer L Slaughter
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Acyclic stereocontrol in the Ireland-Claisen rearrangement of alpha-branched esters.

Authors:  Ying-chuan Qin; Craig E Stivala; Armen Zakarian
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Synthesis of the bis-spiroacetal moiety of spirolides B and D.

Authors:  Kai Meilert; Margaret A Brimble
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

7.  Fragmentation of carbonyl oxides by N-oxides: an improved approach to alkene ozonolysis.

Authors:  Chris Schwartz; Joseph Raible; Kyle Mott; Patrick H Dussault
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

8.  Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization.

Authors:  Daniel P Furkert; Margaret A Brimble
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

9.  Studies on the synthesis of (-)-gymnodimine. Subunit synthesis and coupling.

Authors:  James D White; Laura Quaranta; Guoqiang Wang
Journal:  J Org Chem       Date:  2007-01-31       Impact factor: 4.354

10.  Studies toward a marine toxin immunogen: enantioselective synthesis of the spirocyclic imine of (-)-gymnodimine.

Authors:  Ke Kong; Ziad Moussa; Daniel Romo
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005
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  9 in total

1.  Studies toward the synthesis of maoecrystal V.

Authors:  Zhenhua Gu; Armen Zakarian
Journal:  Org Lett       Date:  2011-01-27       Impact factor: 6.005

Review 2.  Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins.

Authors:  Craig E Stivala; Evelyne Benoit; Rómulo Aráoz; Denis Servent; Alexei Novikov; Jordi Molgó; Armen Zakarian
Journal:  Nat Prod Rep       Date:  2015-03       Impact factor: 13.423

3.  Studies toward the synthesis of spirolide C: exploration into the formation of the 23-membered all-carbon macrocyclic framework.

Authors:  Craig E Stivala; Zhenhua Gu; Lindsay L Smith; Armen Zakarian
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

4.  Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries.

Authors:  Craig E Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2011-07-15       Impact factor: 15.419

5.  An efficient synthesis of the fully elaborated isoindolinone unit of muironolide A.

Authors:  Qing Xiao; Kyle Young; Armen Zakarian
Journal:  Org Lett       Date:  2013-06-13       Impact factor: 6.005

6.  Marine Toxins with Spiroimine Rings: Total Synthesis of Pinnatoxin A.

Authors:  Stéphane Beaumont; Elizabeth A Ilardi; Nicholas D C Tappin; Armen Zakarian
Journal:  European J Org Chem       Date:  2010-10-01

7.  Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.

Authors:  Ke Kong; Ziad Moussa; Changsuk Lee; Daniel Romo
Journal:  J Am Chem Soc       Date:  2011-11-16       Impact factor: 15.419

8.  Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.

Authors:  Tyler J Fulton; Alexander Q Cusumano; Eric J Alexy; Yun E Du; Haiming Zhang; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419

9.  Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.

Authors:  Kaushalendra Patel; Veeranjaneyulu Lanke; Ilan Marek
Journal:  J Am Chem Soc       Date:  2022-04-12       Impact factor: 16.383
  9 in total

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