Literature DB >> 23692417

Synthesis and structure revision of the C43-C67 part of amphidinol 3.

Makoto Ebine1, Mitsunori Kanemoto, Yoshiyuki Manabe, Yosuke Konno, Ken Sakai, Nobuaki Matsumori, Michio Murata, Tohru Oishi.   

Abstract

Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of AM3 was revised from R to S.

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Year:  2013        PMID： 23692417     DOI： 10.1021/ol401176a

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


  4 in total

1.  Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical-Shift Analysis: Insights into their Mechanism of Action.

Authors:  Amanda L Waters; Joonseok Oh; Allen R Place; Mark T Hamann
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-16       Impact factor: 15.336

2.  Karlotoxin synthetic studies: concise synthesis of a C(42-63) B-ring tetrahydropyran fragment.

Authors:  Takashi Tomioka; Yusuke Takahashi; Toshihide Maejima; Yuki Yabe; Hiroki Iwata; Mark T Hamann
Journal:  Tetrahedron Lett       Date:  2013-11-01       Impact factor: 2.415

3.  A highly convergent synthesis of the C1-C31 polyol domain of amphidinol 3 featuring a TST-RCM reaction: confirmation of the revised relative stereochemistry.

Authors:  Aleksandr Grisin; P Andrew Evans
Journal:  Chem Sci       Date:  2015-08-06       Impact factor: 9.825

4.  Channel Formation and Membrane Deformation via Sterol-Aided Polymorphism of Amphidinol 3.

Authors:  Masayuki Iwamoto; Ayumi Sumino; Eri Shimada; Masanao Kinoshita; Nobuaki Matsumori; Shigetoshi Oiki
Journal:  Sci Rep       Date:  2017-09-07       Impact factor: 4.379
  4 in total

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