Synthesis of a pladienolide B analogue with the fully functionalized core structure |
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Authors: | Müller Sarah Mayer Timo Sasse Florenz Maier Martin E |
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Institution: | Institut fu?r Organische Chemie, Universita?t Tu?bingen, Auf der Morgenstelle 18, 72076 Tu?bingen, Germany. |
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Abstract: | Starting from (R)-(-)-linalool (6), terminus differentiation and chain extension via aldol type reactions led to ketophosphonate 16 (C1-C8 building block). In a Horner-Wadsworth-Emmons reaction, 16 reacted with aldehyde 22, which contained the vicinal anti-Me-OH pattern and a vinyl iodide function, to provide the C1-C13 part of pladienolide B. After Shiina macrolactonization, reduction of the enone 26 gave the core structure 27. A Stille cross-coupling of vinyl iodide 27 with tributylphenylstannane eventually furnished analogue 30. |
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