岩沙海葵毒素A、B和C的C(1-6)和C(19-24)片段的合成

Syntheses of the C(1-6) and C(19-24) fragments of lituarines A, B, and C.

作者信息

Robertson Jeremy, Dallimore Jonathan W P, Meo Paul

机构信息

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.

出版信息

Org Lett. 2004 Oct 14;6(21):3857-9. doi: 10.1021/ol048396x.

DOI:10.1021/ol048396x

PMID:15469367

Abstract

[structure: see text] Lituarines A-C are marine natural products comprising a tricyclic spiroacetal bridged at C(8) and C(18) by a functionalized ester linkage conceptually obtained from a C(19-24) alcohol and a C(1-6) carboxylic acid whose oxidation level varies at C(4) and C(5). Stereoselective routes are described to compounds 26 and 27, fully functionalized ester fragments of lituarine A and lituarines B and C, respectively.

摘要

[结构：见正文] 锂盐A - C是海洋天然产物，由一个三环螺缩醛组成，该螺缩醛在C(8)和C(18)处通过一个官能化酯键桥连，从概念上讲，该酯键由一个C(19 - 24)醇和一个C(1 - 6)羧酸得到，其氧化态在C(4)和C(5)处有所不同。本文描述了分别用于制备化合物26和27的立体选择性路线，化合物26和27分别是锂盐A以及锂盐B和C的完全官能化酯片段。