Synthesis of a pladienolide B analogue with the fully functionalized core structure.

Sarah Müller, Timo Mayer, Florenz Sasse, Martin E Maier

Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.

Organic letters 2011 Aug 5

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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. © 2011 American Chemical Society

Citation

Sarah Müller, Timo Mayer, Florenz Sasse, Martin E Maier. Synthesis of a pladienolide B analogue with the fully functionalized core structure. Organic letters. 2011 Aug 5;13(15):3940-3