MISC

1998年9月

Stereocontrolled total synthesis of hemibrevetoxin B

JOURNAL OF ORGANIC CHEMISTRY
  • Kadota, I
  • ,
  • Y Yamamoto

63
19
開始ページ
6597
終了ページ
6606
記述言語
英語
掲載種別
DOI
10.1021/jo9807619
出版者・発行元
AMER CHEMICAL SOC

The stereocontrolled total synthesis of hemibrevetoxin B (1) has been achieved in 56 steps and 0.75% overall yield from D-mannose. The intramolecular reaction of gamma-alkoxyallylstannane with. aldehyde is a key step for the present total synthesis. Thus, the BF3. OEt2-mediated reaction of 24 gave 6 as a sole product. We encountered difficulty in the synthesis of gamma-alkoxyallylstannane 30 from the corresponding allyl ether 29 in which the gamma-alkoxy substituent became sterically quite bulky. This problem was solved by developing the acetal cleavage method for the synthesis of gamma-alkoxyallylstannanes. The cyclization of 38 proceeded smoothly to give the key intermediate 5 in a highly stereoselective manner. Construction of the alpha-vinyl aldehyde and (Z)-diene moieties were performed using Nicolaou's protocol.

リンク情報
DOI
https://doi.org/10.1021/jo9807619
CiNii Articles
http://ci.nii.ac.jp/naid/80010557977
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000076233400036&DestApp=WOS_CPL
ID情報
  • DOI : 10.1021/jo9807619
  • ISSN : 0022-3263
  • CiNii Articles ID : 80010557977
  • Web of Science ID : WOS:000076233400036

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