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Literature DB >> 16146389

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

Abstract

[reaction: see text] The synthesis of the C9-C26 portion of amphidinolide B1 is described. A Fleming allylation followed by elimination was employed for the construction of the C13-C15 diene portion. Sharpless asymmetric dihydroxylation was utilized for regioselective functionalization of a styrene-derived alkene, in the presence of the C13-C15 diene functionality. A highly diastereoselective aldol reaction was developed to establish the C18 stereochemistry.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2005 PMID： 16146389 PMCID： PMC2414262 DOI： 10.1021/ol051544e

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

19 in total

1. Application of the Sharpless Asymmetric Dihydroxylation Methodology to the Enantioselective Preparation of 2,3-Dihydroxytetrahydro-2-naphthoic Esters.

Authors: Lewis N. Mander; Jonathan C. Morris
Journal: J Org Chem Date: 1997-10-17 Impact factor: 4.354

2. Total synthesis of proposed amphidinolide A via a highly selective ring-closing metathesis.

Authors: Robert E Maleczka; Lamont R Terrell; Feng Geng; Joseph S Ward
Journal: Org Lett Date: 2002-08-22 Impact factor: 6.005

3. Unified synthesis of C19-C26 subunits of amphidinolides B1, B2, and B3 by exploiting unexpected stereochemical differences in Crimmins' and Evans' aldol reactions.

Authors: Wei Zhang; Rich G Carter; Alexandre F T Yokochi
Journal: J Org Chem Date: 2004-04-02 Impact factor: 4.354

4. Stereoselective assembly of a 1,3-diene via coupling between an allenic acetate and a (B)-alkylborane: synthetic studies on amphidinolide B1.

Authors: Amit K Mandal; John S Schneekloth; Craig M Crews
Journal: Org Lett Date: 2005-08-18 Impact factor: 6.005

5. Ruthenium-catalyzed alkene-alkyne coupling: synthesis of the proposed structure of amphidinolide A.

Authors: Barry M Trost; John D Chisholm; Stephen T Wrobleski; Michael Jung
Journal: J Am Chem Soc Date: 2002-10-23 Impact factor: 15.419

6. Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations.

Authors: Elizabeth A Colby; Karen C O'Brien; Timothy F Jamison
Journal: J Am Chem Soc Date: 2005-03-30 Impact factor: 15.419

7. Alkene-alkyne coupling as a linchpin: an efficient and convergent synthesis of amphidinolide P.

Authors: Barry M Trost; Julien P N Papillon
Journal: J Am Chem Soc Date: 2004-10-27 Impact factor: 15.419

8. Enantioselective total synthesis of (+)-amphidinolide t1.

Authors: Arun K Ghosh; Chunfeng Liu
Journal: J Am Chem Soc Date: 2003-03-05 Impact factor: 15.419

9. Structure elucidation of (+)-amphidinolide a by total synthesis and NMR chemical shift analysis.

Authors: Barry M Trost; Paul E Harrington
Journal: J Am Chem Soc Date: 2004-04-28 Impact factor: 15.419

10. Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin: asymmetric glycolate aldol reactions and biological evaluation.

Authors: Merritt B Andrus; Erik L Meredith; Erik J Hicken; Bryon L Simmons; Russell R Glancey; Wei Ma
Journal: J Org Chem Date: 2003-10-17 Impact factor: 4.354

6 in total

6. Total Synthesis of Potent Antitumor Macrolide, (-)-Zampanolide: An Oxidative Intramolecular Cyclization-Based Strategy.

Authors: Arun K Ghosh; Xu Cheng; Ruoli Bai; Ernest Hamel
Journal: European J Org Chem Date: 2012-07-01