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Literature DB >> 22720980

Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.

Abstract

Progress toward the synthesis of the microtubule-stabilizing agent, (-)-zampanolide, is reported. Construction of the 2,6-cis-tetrahydropyran ring was accomplished utilizing ether transfer methodology in conjunction with an intramolecular radical cyclization reaction. Efficient installation of the C16-C20 side chain relied on a one-pot cross-metathesis/olefination sequence, Sharpless epoxidation, and selective reduction of a vinyl epoxide.

Entities: CellLine Chemical Disease Species

Mesh：

Substances：
Macrolides
zampanolide

Year: 2012 PMID： 22720980 PMCID： PMC3391338 DOI： 10.1021/ol301383a

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

28 in total

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4. N-Heterocyclic carbene catalyzed oxidative macrolactonization: total synthesis of (+)-dactylolide.

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5. Application of stereoselective ether transfer to the synthesis of isotactic polyethers.

Authors: Kai Liu; Joseph W Arico; Richard E Taylor
Journal: J Org Chem Date: 2010-06-18 Impact factor: 4.354

6. Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.

Authors: Arun K Ghosh; Xu Cheng
Journal: Org Lett Date: 2011-07-12 Impact factor: 6.005

7. Total synthesis of (+)-dactylolide.

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Journal: Org Lett Date: 2005-07-07 Impact factor: 6.005

8. Spongipyran Synthetic Studies. Total Synthesis of (+)-Spongistatin 2.

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Journal: Tetrahedron Date: 2009-08-15 Impact factor: 2.457

9. Alkyne-enol ether cross-metathesis in the presence of CuSO(4): direct formation of 3-substituted crotonaldehydes in aqueous medium.

Authors: Daniele Castagnolo; Lorenzo Botta; Maurizio Botta
Journal: J Org Chem Date: 2009-04-17 Impact factor: 4.354

10. Ruthenium-catalyzed tandem cross-metathesis/Wittig olefination: generation of conjugated dienoic esters from terminal olefins.

Authors: Ryan P Murelli; Marc L Snapper
Journal: Org Lett Date: 2007-03-31 Impact factor: 6.005

6 in total

1. Concise enantioselective synthesis of diospongins A and B.

Authors: Eric Stefan; Ansel P Nalin; Richard E Taylor
Journal: Tetrahedron Date: 2013-09-09 Impact factor: 2.457

2. Synthesis, conformational preferences, and biological activity of conformational analogues of the microtubule-stabilizing agents, (-)-zampanolide and (-)-dactylolide.

Authors: Jeffrey L Henry; Matthew R Wilson; Michael P Mulligan; Taylor R Quinn; Dan L Sackett; Richard E Taylor
Journal: Medchemcomm Date: 2019-04-09 Impact factor: 3.597