Stereocontrolled formal synthesis of (±)-platensimycin
Stereocontrolled formal synthesis of (±)-platensimycin
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DOI：
10.1021/ol801584r
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发表时间：
2008-09-18
期刊：
影响因子：
5.2
通讯作者：
Ishibashi, Hiroyuki
中科院分区：
文献类型：
--
作者：
Matsuo, Jun-ichi;Takeuchi, Kosuke;Ishibashi, Hiroyuki
通过γ-苯甲酰氧基烯酮与叔丁基二甲基异戊二烯的非对映选择性Diels-Alder反应，分子内催化氧化钯化反应生成二氢吡喃环，单硫缩醛与氢化三丁基锡和AIBN的跨环自由基环化反应，立体选择性地合成了具有笼状结构的Platensimycin（Nicolaou全合成Platensimycin的关键中间体）。
The caged structure of platensimycin, known as Nicolaou's key intermediate for total synthesis of platensimycin, was synthesized stereoselectively by using the following key steps: (i) diastereoselective Diels-Alder reaction between gamma-benzoyloxy enone and tert-butyldimethylsiloxydiene, (ii) formation of a dihydropyran ring by intramolecular catalytic oxypalladation, and (iii) transannular radical cyclization of monothloacetal with tributyltin hydride and AIBN.