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Literature DB >> 23543877

Studies Toward the Synthesis of (-)-Zampanolide: Preparation of the Macrocyclic Core.

Dawn M Troast¹, Jiayi Yuan, John A Porco.

Abstract

Studies towards the synthesis of the macrocyclic core of (-)-zampanolide are reported. The synthetic approach features a one-pot reduction/vinylogous aldol reaction for construction of the C15-C20 fragment, an intramolecular silyl-modified Sakurai (ISMS) reaction for construction of the 2,6-cis-disubstituted exo-methylene pyran subunit, and use of an sp2-sp3 Stille reaction for macrocyclization.

Entities: CellLine Chemical Disease Gene Species

Keywords: ISMS; Stille reaction; allyl silane; exo-methylene pyran; macrolide; sp2–sp3 coupling; vinylogous aldol; zampanolide

Year: 2008 PMID： 23543877 PMCID： PMC3612024 DOI： 10.1002/adsc.200800247

Source DB: PubMed Journal: Adv Synth Catal ISSN： 1615-4150 Impact factor: 5.837

25 in total

1. Synthesis and diastereoselective reactions of n,n-dibenzylamino aldehydes and related compounds.

Authors: M T Reetz
Journal: Chem Rev Date: 1999-05-12 Impact factor: 60.622

2. Total synthesis of (+)-zampanolide.

Authors: A B Smith; I G Safonov; R M Corbett
Journal: J Am Chem Soc Date: 2001-12-12 Impact factor: 15.419

3. The N-hydroxymethyl group for stereoselective conjugate addition: application to the synthesis of (-)-statine.

Authors: Dongwon Yoo; Joon Seok Oh; Young Gyu Kim
Journal: Org Lett Date: 2002-04-04 Impact factor: 6.005

4. Total synthesis of (+)-dactylolide.

Authors: Amos B Smith; Igor G Safonov
Journal: Org Lett Date: 2002-02-21 Impact factor: 6.005

5. Total synthesis of (+)-dactylolide through an efficient sequential Peterson olefination and Prins cyclization reaction.

Authors: Danielle L Aubele; Shuangyi Wan; Paul E Floreancig
Journal: Angew Chem Int Ed Engl Date: 2005-05-30 Impact factor: 15.336

6. Intermolecular Heck-type coupling of aryl iodides and allylic acetates.

Authors: Brian Mariampillai; Christelle Herse; Mark Lautens
Journal: Org Lett Date: 2005-10-13 Impact factor: 6.005

7. Preparation and properties of steroidal 17,20- and 20,21-acetonides epimeric at C-20. I. Derivatives of 5beta-pregnan-3alpha-o1.

Authors: M L Lewbart; J J Schneider
Journal: J Org Chem Date: 1969-11 Impact factor: 4.354

8. A convergent synthesis of the tricyclic architecture of the guanacastepenes featuring a selective ring fragmentation.

Authors: William D Shipe; Erik J Sorensen
Journal: Org Lett Date: 2002-06-13 Impact factor: 6.005

9. Efficient and practical method for synthesizing optically active indan-2-ols by the Ti(O-i-Pr)(4)/2 i-PrMgCl-mediated metalative Reppe reaction.

Authors: Takeshi Hanazawa; Kousuke Sasaki; Yuuki Takayama; Fumie Sato
Journal: J Org Chem Date: 2003-06-13 Impact factor: 4.354

Studies Toward the Synthesis of (-)-Zampanolide: Preparation of the Macrocyclic Core.

1. Synthesis and diastereoselective reactions of n,n-dibenzylamino aldehydes and related compounds.

2. Total synthesis of (+)-zampanolide.

3. The N-hydroxymethyl group for stereoselective conjugate addition: application to the synthesis of (-)-statine.

4. Total synthesis of (+)-dactylolide.

5. Total synthesis of (+)-dactylolide through an efficient sequential Peterson olefination and Prins cyclization reaction.

6. Intermolecular Heck-type coupling of aryl iodides and allylic acetates.

7. Preparation and properties of steroidal 17,20- and 20,21-acetonides epimeric at C-20. I. Derivatives of 5beta-pregnan-3alpha-o1.

8. A convergent synthesis of the tricyclic architecture of the guanacastepenes featuring a selective ring fragmentation.

9. Efficient and practical method for synthesizing optically active indan-2-ols by the Ti(O-i-Pr)(4)/2 i-PrMgCl-mediated metalative Reppe reaction.

10. Macrolactonization via Ti(IV)-mediated epoxy-acid coupling: a total synthesis of (-)-dactylolide [and zampanolide].

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

2. Diastereoselectivity in Lewis-acid-catalyzed Mukaiyama aldol reactions: a DFT study.

3. Stereoselective synthesis of spirocyclic oxindoles via Prins cyclizations.

Review 4. Zampanolide and dactylolide: cytotoxic tubulin-assembly agents and promising anticancer leads.