Total Synthesis of 2′",5′"-Diepisilvestrol and Its C1′" Epimer: Key Structure Activity Relationships at C1′" and C2′"

被引：19
|
作者：
Chambers, Jennifer M. [1 ]
Huang, David C. S. [2 ,3 ]
Lindqvist, Lisa M. [2 ,3 ]
Savage, G. Paul [4 ]
White, Jonathan M. [1 ]
Rizzacasa, Mark A. [1 ]
机构：
[1] Univ Melbourne, Inst Bio21, Sch Chem, Melbourne, Vic 3010, Australia
[2] Univ Melbourne, Dept Med Biol, Melbourne, Vic 3010, Australia
[3] Walter & Eliza Hall Inst Med Res, Parkville, Vic 3052, Australia
[4] CSIRO Mol & Hlth Technol, Melbourne, Vic 3168, Australia
来源：
JOURNAL OF NATURAL PRODUCTS | 2012年 / 75卷 / 08期
基金：
澳大利亚研究理事会; 英国医学研究理事会;
关键词：
SILVESTROL; (-)-EPISILVESTROL; DERIVATIVES;
D O I：
10.1021/np300376f
中图分类号：
Q94 [植物学];
学科分类号：
071001 ;
摘要：
The first total synthesis of the low-abundance natural product 2''',5'''-diepisilvestrol (4) is described. The key step involved a Mitsunobu coupling between cyclopenta[b]-benzofuran phenol 7 and dioxane lactol 6. Deprotection then gave a 1:2.6 ratio of natural product 2''',5'''-diepisilvestrol (4) and its C1 epimer 1''',2''',5'''-triepisilvestrol (15) in 50% overall yield. An in vitro protein translation inhibition assay showed that 2''',5'''-diepisilvestrol (4) was considerably less active than episilvestrol (2), while the unnatural isomer 1''',2''',5'''-triepisilvestrol (15) was essentially inactive, showing that the configuration at C1''' and C2'''. has a large effect on the biological activity.
引用
收藏
页码：1500 / 1504
页数：5
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