Synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1: an iodoetherification-dehydroiodination strategy for complex spiroketals.
Synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1: an iodoetherification-dehydroiodination strategy for complex spiroketals.
复制标题
azaspiracid-1 的 ABCD 三氧二螺缩酮亚基的合成：复杂螺缩酮的碘醚化-脱碘氢化策略。
DOI：
10.1021/ol701866v
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发表时间：
2007
期刊：
影响因子：
5.2
通讯作者：
Mootoo,DavidR
中科院分区：
文献类型：
--
作者：
Li,Xiaohua;Li,Jialiang;Mootoo,DavidR
一种不寻常的螺缩酮化策略，其中羟基烯烃作为前体的环状烯醇醚应用于合成的ABCD三恶二螺缩酮亚基azaspiracid-1。代表双异头效应的三恶二螺缩酮产物作为单一三恶二螺缩酮非对映异构体获得。CD片段合成中的一个关键策略是使用环丙烷作为C-14甲基的合成子。
An unusual spiroketalization strategy in which a hydroxyalkene serves as a precursor to a cyclic enol ether was applied to the synthesis of the ABCD trioxadispiroketal subunit of azaspiracid-1. The trioxadispiroketal product, which represents a double anomeric effect, was obtained as a single trioxadispiroketal diastereomer. A key ploy in the synthesis of the CD segment was the use of a cyclopropane as a synthon for the C-14 methyl group.