抄録
The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol derivative 7, followed by Zn[BH 4] 2 reduction. Comparison of the spectroscopic data of the synthetic (±)-1 and (±)-13 resulted in structural revision of the natural calafianin to 13, possessing the trans-relationship between an epoxide and an oxygen of the isoxazoline. In addition, a significant difference of antimicrobial activity between 1 and 13 is discussed.
| 元の言語 | English |
|---|---|
| ページ（範囲） | 134-139 |
| ページ数 | 6 |
| ジャーナル | Bulletin of the Chemical Society of Japan |
| 巻 | 79 |
| 発行部数 | 1 |
| DOI | |
| 出版物ステータス | Published - 2006 |
Fingerprint
ASJC Scopus subject areas
- Chemistry(all)
これを引用
Total synthesis, structural revision, and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni. / Ogamino, Takahisa; Obata, Rika; Tomoda, Hiroshi; Nishiyama, Shigeru.
：: Bulletin of the Chemical Society of Japan, 巻 79, 番号 1, 2006, p. 134-139.研究成果: Article
}
TY - JOUR
T1 - Total synthesis, structural revision, and biological evaluation of calafianin, a marine spiroisoxazoline from the sponge, Aplysina gerardogreeni
AU - Ogamino, Takahisa
AU - Obata, Rika
AU - Tomoda, Hiroshi
AU - Nishiyama, Shigeru
PY - 2006
Y1 - 2006
N2 - The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol derivative 7, followed by Zn[BH 4] 2 reduction. Comparison of the spectroscopic data of the synthetic (±)-1 and (±)-13 resulted in structural revision of the natural calafianin to 13, possessing the trans-relationship between an epoxide and an oxygen of the isoxazoline. In addition, a significant difference of antimicrobial activity between 1 and 13 is discussed.
AB - The reported structure of the natural calafianin (1) and its isomer in the epoxide region 13 were successfully synthesized through the cis- and trans-spiroisoxazoline compounds, which were produced by electrochemical oxidation of the hydroxyimino-phenol derivative 7, followed by Zn[BH 4] 2 reduction. Comparison of the spectroscopic data of the synthetic (±)-1 and (±)-13 resulted in structural revision of the natural calafianin to 13, possessing the trans-relationship between an epoxide and an oxygen of the isoxazoline. In addition, a significant difference of antimicrobial activity between 1 and 13 is discussed.
UR - http://www.scopus.com/inward/record.url?scp=33750506090&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33750506090&partnerID=8YFLogxK
U2 - 10.1246/bcsj.79.134
DO - 10.1246/bcsj.79.134
M3 - Article
AN - SCOPUS:33750506090
VL - 79
SP - 134
EP - 139
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 1
ER -