Synthetic approaches for the elucidation of structure, conformation and functions of an antifungal natural product amphidinol 3

2014 Fiscal Year Final Research Report

• Project/Area Number: 24750092
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Kyushu University
• Principal Investigator: EBINE Makoto 九州大学, 理学(系)研究科(研究院), 助教 (70545574)
• Co-Investigator(Renkei-kenkyūsha): OISHI Tohru 九州大学, 大学院理学(系)研究科(研究院), 教授 (90241520)
• Research Collaborator: UMEDA Aya ; TSURUDA Takeshi ; OMIZU Hiroyuki ; TAKADA Yuri ; WAKAMIYA Yuma ; YANAI Naoto
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: アンフィジノール３ / 合成研究 / 構造確認 / ポリエン―ポリオール系抗真菌剤

Outline of Final Research Achievements

We carried out the synthetic studies on amphidinol 3, an antifungal polyene-polyol compound isolated from marine dinoflagellate amphidinium klebsii. Although many researchers have been concentrated on the synthetic studies of amphidinol 3, total synthesis of amphidinol 3 has not yet been achieved.
We synthesized the C43-C67 part of amphidinoil 3 and its C51 diastereomer. Through the comparison of their 1H and 13C NMR spectra with those of natural amphidinol 3, we concluded the stereochemistry at C51 should be revised.
We also established the synthetic route for the three requisite parts, i.e., polyhydroxy part (C1-C29), bis-THP part (C30-C52), and polyene part (C53-C67). We are now trying to unite these parts to complete the total synthesis of the proposed structure of amphidinol 3.

Free Research Field

有機合成化学、天然物化学