Literature DB >> 15969572

Total synthesis of RK-397.

Scott E Denmark1, Shinji Fujimori.   

Abstract

An enantioselective synthesis of the polyene macrolide RK-397 is described. The use of the same eight-carbon building block twice for the construction of the polyol chain allowed for a highly convergent synthesis. The synthesis highlights stereoselective vinylogous aldol addition using a chiral bisphosphoramide as well as a sequential palladium-catalyzed cross-coupling reaction for the preparation of key fragments.

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Year:  2005        PMID: 15969572     DOI: 10.1021/ja052226d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

1.  Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates.

Authors:  Scott E Denmark; Andrea Ambrosi
Journal:  Org Process Res Dev       Date:  2015       Impact factor: 3.317

2.  Total synthesis and biological evaluation of monorhizopodin and 16-epi-monorhizopodin.

Authors:  K C Nicolaou; Xuefeng Jiang; Peter J Lindsay-Scott; Andrei Corbu; Sawako Yamashiro; Andrea Bacconi; Velia M Fowler
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-07       Impact factor: 15.336

3.  Total synthesis of (+)-roxaticin via C-C bond forming transfer hydrogenation: a departure from stoichiometric chiral reagents, auxiliaries, and premetalated nucleophiles in polyketide construction.

Authors:  Soo Bong Han; Abbas Hassan; In Su Kim; Michael J Krische
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

4.  De novo synthesis of 2-substituted syn-1,3-diols via an iterative asymmetric hydration strategy.

Authors:  Md Moinuddin Ahmed; Matthew S Mortensen; George A O'Doherty
Journal:  J Org Chem       Date:  2006-09-29       Impact factor: 4.354

5.  Synthesis of C1-C20 and C21-C40 fragments of tetrafibricin.

Authors:  Venugopal Gudipati; Dennis P Curran
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

Review 6.  De novo synthesis of natural products via the asymmetric hydration of polyenes.

Authors:  Yanping Wang; Yalan Xing; Qi Zhang; George A O'Doherty
Journal:  Chem Commun (Camb)       Date:  2011-05-11       Impact factor: 6.222

7.  Cyclic Acetal Formation Between 2-Pyridinecarboxaldehyde and gamma-Hydroxy-alpha,beta-Acetylenic Esters.

Authors:  Sami Osman; Kazunori Koide
Journal:  Tetrahedron Lett       Date:  2008-11-10       Impact factor: 2.415

8.  Improved total synthesis of the potent HDAC inhibitor FK228 (FR-901228).

Authors:  Thomas J Greshock; Deidre M Johns; Yasuo Noguchi; Robert M Williams
Journal:  Org Lett       Date:  2008-01-19       Impact factor: 6.005

9.  The interplay of invention, discovery, development, and application in organic synthetic methodology: a case study.

Authors:  Scott E Denmark
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

10.  Palladium-catalyzed cross-coupling reactions of organosilanols and their salts: practical alternatives to boron- and tin-based methods.

Authors:  Scott E Denmark; Christopher S Regens
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

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