Literature DB >> 14507177

Total synthesis of scytophycin C. 1. Stereoselective syntheses of the C(1)-C(18) segment and the C(19)-C(31) segment.

Ryoichi Nakamura1, Keiji Tanino, Masaaki Miyashita.   

Abstract

[structure: see text] Stereoselective total synthesis of scytophycin C, a marine 22-membered macrolide displaying potent activity against a variety of human carcinoma cell lines, has been reported in which the polypropionate structure bearing contiguous asymmetric centers was stereospecifically constructed by using new acyclic stereocontrol. This paper describes stereoselective syntheses of the C(1)-C(18) segment (Segment A) including a trans-disubstituted dihydropyran ring and the C(19)-C(31) segment (Segment B) having eight stereogenic centers.

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Year:  2003        PMID： 14507177     DOI： 10.1021/ol035227o

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


  9 in total

1.  A synthetic entry to pladienolide B and FD-895.

Authors:  Alexander L Mandel; Brian D Jones; James J La Clair; Michael D Burkart
Journal:  Bioorg Med Chem Lett       Date:  2007-07-07       Impact factor: 2.823

2.  Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide construction.

Authors:  Xin Gao; Hoon Han; Michael J Krische
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

3.  Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold.

Authors:  Baudouin Gerard; Jean-Charles Marié; Bhaumik A Pandya; Maurice D Lee; Haibo Liu; Lisa A Marcaurelle
Journal:  J Org Chem       Date:  2011-02-22       Impact factor: 4.354

4.  Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols.

Authors:  Inji Shin; Michael J Krische
Journal:  Org Lett       Date:  2015-10-02       Impact factor: 6.005

Review 5.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

Review 6.  Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal:  Nat Prod Rep       Date:  2014-02-11       Impact factor: 13.423

7.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419

8.  Regioselective Cleavage of 3,4-Epoxy Alcohols with Substituted Alkynylaluminum Reagents: Application to the Stereoselective Synthesis of Polypropionates.

Authors:  Wilnelia Dávila; Wildeliz Torres; José A Prieto
Journal:  Tetrahedron       Date:  2007-08-20       Impact factor: 2.457

9.  Synthesis of an enantiopure isoxazolidine monomer for β-aspartic acid in chemoselective β-oligopeptide synthesis.

Authors:  Hiroshi Ishida; Nancy Carrillo; Jeffrey W Bode
Journal:  Tetrahedron Lett       Date:  2009-07-01       Impact factor: 2.415
  9 in total

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