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

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

Research output: Contribution to journalArticle

17 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2846-2849
Number of pages4
JournalOrganic Letters
Volume15
Issue number11
DOIs
Publication statusPublished - Jun 26 2013

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nuclear magnetic resonance
oxidation
synthesis
configurations
Nuclear magnetic resonance
Oxidation
amphidinol 3

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis and structure revision of the C43-C67 part of amphidinol 3. / Ebine, Makoto; Kanemoto, Mitsunori; Manabe, Yoshiyuki; Konno, Yosuke; Sakai, Ken; Matsumori, Nobuaki; Murata, Michio; Oishi, Tohru.

In: Organic Letters, Vol. 15, No. 11, 26.06.2013, p. 2846-2849.

Research output: Contribution to journalArticle

Ebine, Makoto ; Kanemoto, Mitsunori ; Manabe, Yoshiyuki ; Konno, Yosuke ; Sakai, Ken ; Matsumori, Nobuaki ; Murata, Michio ; Oishi, Tohru. / Synthesis and structure revision of the C43-C67 part of amphidinol 3. In: Organic Letters. 2013 ; Vol. 15, No. 11. pp. 2846-2849.
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