THE BRIARELLINS, NEW EUNICELLIN-BASED DITERPENOIDS FROM A CARIBBEAN GORGONIAN, BRIAREUM-ASBESTINUM

被引：32
作者：
RODRIGUEZ, AD
COBAR, OM
机构：
[1] Department of Chemistry, University of Puerto Rico, U.P.R. Station Río Piedras, 00931-3346
来源：
TETRAHEDRON | 1995年 / 51卷 / 25期
关键词：
D O I：
10.1016/0040-4020(95)00339-A
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Caribbean gorgonian Briareum asbestinum has been shown to contain representatives from three skeletal classes, asbestinins, briareins, and eunicellins. The structural diversity of the diterpenoids isolated suggest a common biosynthetic pathway. Briarellius -A (1), -B (3), -C (5), and -D (6) are members of a new class of tetracyclic diterpenoids of the eunicellin family distinguished by the presence of a seven-membered lactone ring formed between C-3 and C-16. Seco-briarellin e), which possesses a novel carbon skeleton, is the first representative of a new class of ether-cyclized eunicellin diterpenes known as seco-eunicellins. The briarellins are also unique among the compounds in this series in having the opposite relative stereochemistry at C-11 to that found in eunicellin-based compounds isolated from South Pacific soft corals. The structures of the new eunicellin-type diterpenoids were established after extensive analysis of spectral data and those of 3 and 5 were confirmed by chemical interconversions. Briarellin-A (1) displayed modest in vitro cytotoxicity against HeLa cells.
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页码：6869 / 6880
页数：12
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