Smith Amos B, Pitram Suresh M, Fuertes Michael J
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Org Lett. 2003 Jul 24;5(15):2751-4. doi: 10.1021/ol034989g.
[structure: see text] The synthesis of an appropriately functionalized advanced C(1-18) polyol fragment of the mycosamine-glycosylated polyene macrolide, (+)-rimocidin (1), has been achieved in a highly efficient manner. Highlights of the strategy include the S(N)2/S(N)2' addition of dithiane anions to vinyl epoxides and the multicomponent linchpin union of 2-TBS-1,3-dithiane with two advanced epoxides.
[结构:见正文] 高效地实现了霉菌胺糖基化多烯大环内酯(+)-龟裂杀菌素(1)中适当官能化的高级C(1-18)多元醇片段的合成。该策略的亮点包括二硫烷阴离子对乙烯基环氧化物的S(N)2/S(N)2'加成以及2-TBS-1,3-二硫烷与两个高级环氧化物的多组分关键连接。