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Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7
Soraya Manaviazar1, Mark Frigerio, Gurpreet S Bhatia
1UCL Center for Chemical Genomics, Christopher Ingold Laboratories, Chemistry Department, University College London, 20 Gordon Street, London WC1H 0AJ, UK. s.manaviazar@ucl.ac.uk
Abstract:
A new enantioselective synthesis of Masamune's AB fragment (1) for bryostatin 7 is described. Key steps in the new route include a Meerwein-Ponndorf-Verley reduction to set the O(7) stereocenter and an alkylative union between the dithiane 6 and iodide 5 to construct the C(9)-C(10) bond. Because we have previously published a synthesis of Masamune's C-ring phenyl sulfone 2, our new route to 1 constitutes a formal total synthesis of bryostatin 7; it also corrects the previously reported spectral data for 1 in CDCl3.
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