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  Total Synthesis of Amphidinolide X

Lepage, O., Kattnig, E., & Fürstner, A. (2004). Total Synthesis of Amphidinolide X. Journal of the American Chemical Society, 126(49), 15970-15971. doi:10.1021/ja044130+.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-000F-973D-5 Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0028-1434-8
Genre: Journal Article

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[189]SI.pdf (Supplementary material), 2MB
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 Creators:
Lepage, Olivier1, Author              
Kattnig, Egmont1, Author              
Fürstner, Alois1, Author              
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1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              

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 Abstract: A concise total synthesis of the cytotoxic marine natural product amphidinolide X (1) is described. A key step of the highly convergent route to this structurally rather unusual macrodiolide derivative consists of a newly developed, highly syn selective formation of allenol 6 by an iron-catalyzed ring opening reaction of the enantioenriched propargyl epoxide 5 (derived from a Sharpless epoxidation) with a Grignard reagent. Allenol 6 was then cyclized with the aid of Ag(I) to give dihydrofuran 7 containing the (R)-configured quarternary sp3 chiral center at C19 of the target. The anti-configured chiral centers at C10 and C11 were formed by the palladium-catalyzed, Et2Zn-promoted addition of propargyl mesylate 12 to the functionalized aldehyde 11. The key fragment coupling at the C13−C14 bond was achieved by the “9-MeO-9-BBN” variant of the alkyl-Suzuki reaction. Finally, the 16-membered macrodiolide ring was formed by a Yamaguchi esterification/lactonization strategy.

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Language(s): eng - English
 Dates: 2004-09-272004-11-192004-12-15
 Publication Status: Published in print
 Pages: 2
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: eDoc: 219316
DOI: 10.1021/ja044130+
ISI: 000225697000023
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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 126 (49) Sequence Number: - Start / End Page: 15970 - 15971 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870