論文

査読有り
2004年9月

Convergent synthesis of the ABCDE-ring part of ciguatoxin CTX3C

TETRAHEDRON LETTERS
  • K Fujiwara
  • ,
  • A Goto
  • ,
  • D Sato
  • ,
  • Y Ohtaniuchi
  • ,
  • H Tanaka
  • ,
  • A Murai
  • ,
  • H Kawai
  • ,
  • T Suzuki

45
38
開始ページ
7011
終了ページ
7014
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1016/j.tetlet.2004.07.145
出版者・発行元
PERGAMON-ELSEVIER SCIENCE LTD

Convergent synthesis of the ABCDE-ring part (2) of ciguatoxin CTX3C (1) has been achieved. A carbanion stabilized by a dimethyldithioacetal S-oxide group in the AB-ring part (4) readily reacted with an aldehyde group in the E-ring part (5). The resulting adduct was facilely converted to the corresponding beta,gamma-unsaturated alpha,epsilon-dihydroxy ketone (3). The subsequent reductive hydroxy-ketone-cyclization reactions constructed the CD-ring part efficiently. Thus, the ABCDE-ring part (2) was concisely synthesized in 10 steps in 11% overall yield from the AB-ring and the E-ring parts (4 and 5). (C) 2004 Elsevier Ltd. All rights reserved.

リンク情報
DOI
https://doi.org/10.1016/j.tetlet.2004.07.145
CiNii Articles
http://ci.nii.ac.jp/naid/80016847486
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000223814500004&DestApp=WOS_CPL
ID情報
  • DOI : 10.1016/j.tetlet.2004.07.145
  • ISSN : 0040-4039
  • CiNii Articles ID : 80016847486
  • Web of Science ID : WOS:000223814500004

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