Gaunt Matthew J, Jessiman Alan S, Orsini Paolo, Tanner Huw R, Hook David F, Ley Steven V
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK.
Org Lett. 2003 Dec 11;5(25):4819-22. doi: 10.1021/ol035849+.
The synthesis of the C-1-C-28 ABCD fragment of spongistatin is described. Anti-selective boron-mediated aldol coupling of a CD spiroketal ketone fragment to an AB spiroketal aldehyde unit forms the desired C1-C28 advanced intermediate. Other features include the double conjugate addition of a dithiol to an ynone to generate the key beta-keto-dithiane unit required for the synthesis of the AB spiroketal fragment. [reaction: see text]
描述了海绵他汀C-1-C-28 ABCD片段的合成。通过将CD螺缩酮酮片段与AB螺缩酮醛单元进行反选择性硼介导的羟醛偶联反应，形成了所需的C1-C28高级中间体。其他特点包括二硫醇对炔酮的双共轭加成反应，以生成合成AB螺缩酮片段所需的关键β-酮二硫烷单元。[反应：见正文]
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