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

页码：1500 / 1504

页数：5

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