Ghosh Arun K, Lei Hui
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, 60607, USA.
J Org Chem. 2002 Dec 13;67(25):8783-8. doi: 10.1021/jo020402k.
Chelation-controlled reduction of chiral beta-alkoxy ketones containing a competing beta'-oxygen functionality has been investigated. Various syn-1,3-diols were prepared conveniently by reduction of beta-alkoxy ketones with LiI/LiAlH(4) (syn:anti selectivity up to >99:1). The corresponding beta-alkoxy ketones were derived from nitro-aldol reactions of chiral alkoxy aldehydes with a series of nitro compounds. This methodology is utilized in a short and efficient synthesis of the delta-lactone moiety of the HMG-CoA reductase inhibitors compactin and mevinolin.
已对含有竞争β'-氧官能团的手性β-烷氧基酮的螯合控制还原进行了研究。通过用LiI/LiAlH₄还原β-烷氧基酮方便地制备了各种顺式-1,3-二醇（顺式：反式选择性高达>99:1）。相应的β-烷氧基酮衍生自手性烷氧基醛与一系列硝基化合物的硝基羟醛反应。该方法用于高效简短合成HMG-CoA还原酶抑制剂洛伐他汀和辛伐他汀的δ-内酯部分。
