Total Synthesis of 2 &#39;&#39;&#39;,5 &#39;&#39;&#39;-Diepisilvestrol and Its C1 &#39;&#39;&#39; Epimer: Key Structure Activity Relationships at C1 &#39;&#39;&#39; and C2 &#39;&#39;&#39;

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

Author(s): Chambers, JM; Huang, DCS; Lindqvist, LM; Savage, GP; White, JM; Rizzacasa, MA;
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
Research Division(s): Chemical Biology
Publisher's Version: https://doi.org/10.1021/np300376f

Creation Date: 2012-08-01 12:00:00