STEREOCONTROLLED 2ND GENERATION SYNTHESES OF THE ABC AND FG RING-SYSTEMS OF BREVETOXIN-B
STEREOCONTROLLED 2ND GENERATION SYNTHESES OF THE ABC AND FG RING-SYSTEMS OF BREVETOXIN-B
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DOI：
10.1016/s0040-4020(01)85579-4
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发表时间：
1990-01-01
期刊：
影响因子：
2.1
通讯作者：
HWANG, CK
中科院分区：
文献类型：
--
作者：
NICOLAOU, KC;NUGIEL, DA;HWANG, CK
描述了短尾毒素 B (1) ABC 和 FG 环系统的立体控制第二代合成。代表ABC和FG环框架的两个关键中间体2和3是由2-脱氧-D-核糖通过短而有效的序列制备的。 2的合成通过环氧醇环化前体6和7以及Horner-Emmons环化前体5进行，以3.6%的总产率得到所需的三环体系。 3的合成通过环氧醇环化前体10和11进行，以11.5%的总产率得到所需的双环系统。这两种合成都代表了对之前程序的改进，并允许快速、轻松地进入这种复杂天然产物的 ABC 和 FG 环系统。
Stereocontrolled, second generation synthesis of the ABC and FG ring systems of brevetoxin B (1) are described. The two key intermediates 2 and 3, representing the ABC and FG ring frameworks, were prepared from 2-deoxy-D-ribose via short and efficient sequences. The synthesis of 2 proceeded via the epoxy alcohol cyclization precursors 6 and 7, and the Horner-Emmons cyclization precursor 5, to give the desired tricyclic system in 3.6% overall yield. The synthesis of 3 proceeded via the epoxy alcohol cyclization precursors 10 and 11 to give the desired bicyclic system in a 11.5% overall yield. Both syntheses represent improvements over the previous procedures and allow for rapid and facile entries into the ABC and FG ring systems of this complex natural product.