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• W2055575057 startingPage "15970" @default.
• W2055575057 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." @default.
• W2055575057 created "2016-06-24" @default.
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• W2055575057 date "2004-11-19" @default.
• W2055575057 modified "2023-10-06" @default.
• W2055575057 title "Total Synthesis of Amphidinolide X" @default.
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• W2055575057 doi "https://doi.org/10.1021/ja044130+" @default.
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• W2055575057 hasPublicationYear "2004" @default.
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