Total Synthesis of 2 ''',5 '''-Diepisilvestrol and Its C1 ''' Epimer: Key Structure Activity Relationships at C1 ''' and C2 '''
Details
Publication Year 2012-08, Volume 75, Issue #8, Page 1500-1504
Journal Title
JOURNAL OF NATURAL PRODUCTS
Publication Type
Journal Article
Abstract
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.
Publisher
AMER CHEMICAL SOC
Keywords
MITSUNOBU REACTION; SILVESTROL; (-)-SILVESTROL; (-)-EPISILVESTROL; EPISILVESTROL; ROCAGLAMIDES; DERIVATIVES
WEHI Research Division(s)
Chemical Biology
Publisher's Version
https://doi.org/10.1021/np300376f
Rights Notice
Copyright © 2013 American Chemical Society


Creation Date: 2012-08-01 12:00:00
Last Modified: 0001-01-01 12:00:00
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