格尔德霉素对苯醌区域的选择性合成。

Selective synthesis of the para-quinone region of geldanamycin.

作者信息

Andrus Merritt B, Hicken Erik J, Meredith Erik L, Simmons Bryon L, Cannon John F

机构信息

Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, Utah 84602-5700, USA.

出版信息

Org Lett. 2003 Oct 16;5(21):3859-62. doi: 10.1021/ol035400g.

DOI:10.1021/ol035400g

PMID:14535728

Abstract

[structure: see text] The quinone portion of the ansamycin geldanamycin was made with complete selectivity from the 1,4-dihydroquinone generated from a 1,4-bis-methoxymethyl (MOM) ether intermediate. Palladium catalysis with air gave the desired product in 98% isolated yield. The structure was established using NMR, UV, and X-ray analysis with comparisons to geldanamycin, ortho-quino-geldanamycin and a model compound.

摘要

[结构：见正文] 安莎霉素格尔德霉素的醌部分由1,4-双甲氧基甲基（MOM）醚中间体生成的1,4-二氢醌完全选择性地制备。在空气中进行钯催化，以98%的分离产率得到所需产物。通过核磁共振（NMR）、紫外（UV）和X射线分析，并与格尔德霉素、邻醌格尔德霉素和一种模型化合物进行比较，确定了其结构。