Total Synthesis of Brevetoxin A: Part 3: Construction of GHIJ and BCDE Ring Systems

Pivotal intermediates in the total synthesis of brevetoxin A are the BCDE and the GHIJ ring systems. Several of the previously developed methodologies such as hydroxy epoxide cyclizations, hydroxy dithioketal cyclizations, and Pd‐catalyzed coupling with bis(cyclic ketene acetal phosphates) were empl...

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Published inChemistry : a European journal Vol. 5; no. 2; pp. 628 - 645
Main Authors Nicolaou, K. C., Shi, Guo-qiang, Gunzner, Janet L., Gärtner, Peter, Wallace, Paul A., Ouellette, Michael A., Shi, Shuhao, Bunnage, Mark E., Agrios, Konstantinos A., Veale, Chris A., Hwang, Chan-Kou, Hutchinson, John, Prasad, C. V. C., Ogilvie, William W., Yang, Zhen
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.02.1999
WILEY‐VCH Verlag
Wiley
Subjects
Brevetoxin A
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Synthetic methods
Total synthesis
brevetoxin A
GENERATION STRATEGIES
total synthesis
CYCLIC ETHERS
TECHNOLOGY
synthetic methods
STEREOCONTROLLED SYNTHESIS
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Summary:Pivotal intermediates in the total synthesis of brevetoxin A are the BCDE and the GHIJ ring systems. Several of the previously developed methodologies such as hydroxy epoxide cyclizations, hydroxy dithioketal cyclizations, and Pd‐catalyzed coupling with bis(cyclic ketene acetal phosphates) were employed to achieve these synthetic goals.
Bibliography:ark:/67375/WNG-FJD0H4WM-5
istex:1E5D72CDC0ED16D6FDA4CEB5BBF2BA139C3D9435
ArticleID:CHEM628
ISSN:0947-6539
1521-3765
DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E