二聚体聚酮天然产物SCH 351448的C1-C21（C1'-C21'）片段的合成

Synthesis of the C1-C21 (C1'-C21') fragment of the dimeric polyketide natural product SCH 351448.

作者信息

Bhattacharjee Ashoke, Soltani Omid, De Brabander Jef K

机构信息

Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, Dallas, Texas 75390-9038, USA.

出版信息

Org Lett. 2002 Feb 21;4(4):481-4. doi: 10.1021/ol016938u.

DOI:10.1021/ol016938u

PMID:11843571

Abstract

[structure: see text] A convergent, stereoselective assembly of the C1-C21 (C1'-C21') fragment of SCH 351448, a 28-membered bis-lactone natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

摘要

[结构：见正文] 已开发出一种汇聚式、立体选择性合成SCH 351448（一种28元双内酯天然产物）的C1-C21（C1'-C21'）片段的方法。一种高效合成该片段的方法构建了天然产物中75%的碳骨架和所有立体化学元素。此外，还报道了一种有趣的硼配体对与甲基酮衍生的烯醇硼酸酯进行关键羟醛反应的非对映选择性的影响。