Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section

Tomoyuki Koge, Yuma Wakamiya, Makoto Ebine, Tohru Oishi

Research output: Contribution to journalArticle

Abstract

An artificial analog corresponding to the C31-C67 section of amphidinol 3 (AM3) was designed as a part of the structure-activity relationship studies to elucidate structure requirements for eliciting antifungal activity. To reduce the number of synthetic steps, the 43-deoxy-51-epi derivative containing common tetrahydropyran ring system was designed and synthesized from a pivotal intermediate in 17 steps. The analog elicited no antifungal activity, suggesting that not only the two tetrahydropyran rings, but also polyol section of AM3 are necessary to elicit antifungal activity.

Original languageEnglish
Pages (from-to)1197-1202
Number of pages6
JournalHeterocycles
Volume96
Issue number7
DOIs
Publication statusPublished - Jan 1 2018

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Structure-Activity Relationship
Derivatives
amphidinol 3
polyol

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section. / Koge, Tomoyuki; Wakamiya, Yuma; Ebine, Makoto; Oishi, Tohru.

In: Heterocycles, Vol. 96, No. 7, 01.01.2018, p. 1197-1202.

Research output: Contribution to journalArticle

Koge, Tomoyuki ; Wakamiya, Yuma ; Ebine, Makoto ; Oishi, Tohru. / Synthesis of an analog of amphidinol 3 corresponding to the c31-c67 section. In: Heterocycles. 2018 ; Vol. 96, No. 7. pp. 1197-1202.
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