Asymmetric synthesis of the northern half C1-C16 of the bryostatins.
Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one, the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence). Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.
Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-30167 Hannover, Germany.
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Vakalopoulos
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Lampe
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Hoffmann
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D054713:Bryostatins; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure
D000970:Antineoplastic Agents; D054713:Bryostatins; D007202:Indicators and Reagents; D007783:Lactones; D018942:Macrolides; C046785:bryostatin 1