2007年6月
Synthesis and relative stereochemistry of the A- and F-rings of goniodomin A
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
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- 巻
- 80
- 号
- 6
- 開始ページ
- 1173
- 終了ページ
- 1186
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1246/bcsj.80.1173
- 出版者・発行元
- CHEMICAL SOC JAPAN
The synthesis of the A- and F-rings of goniodomin A (1), which is a stereochemically unidentified antifungal agent isolated from dinoflagellate Alexandrium hiranoi, was performed to determine of the relative stereochemistry of these parts. The relative stereochemistry of the A- and F-rings was first deduced from Murakami's NMR data, and model compounds corresponding to these parts were then synthesized. The synthetic A-ring model, of which the structure was established by X-ray crystallographic analysis, showed good agreement with the natural A-ring on the basis of J and NOE behavior in the H-1 NMR spectroscopy. The chemical shifts in H-1 and C-13 NMR specta and J(32-OH-H33) of the synthetic F-ring model having a 33S,34R configuration also agreed with those of the F-ring of 1. Thus, the relative stereochemistry of the A- and F-rings of 1 was elucidated.
- リンク情報
- ID情報
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- DOI : 10.1246/bcsj.80.1173
- ISSN : 0009-2673
- eISSN : 1348-0634
- CiNii Articles ID : 10019586687
- Web of Science ID : WOS:000248256600017