Second-generation, highly abbreviated route for elaboration of the oxetane D-Ring in a fully functionalized taxane
Second-generation, highly abbreviated route for elaboration of the oxetane D-Ring in a fully functionalized taxane
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DOI：
10.1021/jo0482965
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发表时间：
2005-01-21
影响因子：
3.6
通讯作者：
Paquette, LA
中科院分区：
文献类型：
--
作者：
Brennan, NK;Guo, X;Paquette, LA
报道了环氧乙烷3到氧杂环丁烷9的六步转化。该合成路线特别利用了3在极性反应介质中的酸催化开环为烯丙醇4以及OsO4. TMEDA络合物的提高的能力来实现该中间体的有效立体控制的二羟基化。新序列的总收率为33%。
A six-step conversion of oxirane 3 to oxetane 9 is reported. The synthetic route takes particular advantage of the acid-catalyzed ring opening of 3 to allyl alcohol 4 in a polar reaction medium and of the heightened capability of the OsO4.TMEDA complex to effect the efficient stereocontrolled dihydroxylation of this intermediate. The overall yield of the new sequence is 33%.