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Halichondrin B: Synthesis of the C(1)−C(15) Subunit

✍ Scribed by Burke, Steven D.; Jung, Kyung Woon; Lambert, William T.; Phillips, Jeannie R.; Klovning, Jason J.


Book ID
126205242
Publisher
American Chemical Society
Year
2000
Tongue
English
Weight
359 KB
Volume
65
Category
Article
ISSN
0022-3263

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An expeditious synthesis of the C(1)-C(1
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The synthesis of he C(l)-C(14) segment 1 of hakhondtin B was achieved efficient&. Featured are the pinacof rearrangement of a-hydroxymesylate 0. the intramolecular Michael addition of 11, and the one-pot muftfstep mnversion of 73 to 1.

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A concise route to the C1-C15 domain of the halichondrins is described. The key reaction is the conversion of a furfuryl alcohol to a pyranone. The stereocenter of this pyranone serves as the starting point for the other 8 stereocenters.