SYNTHESES VIA VINYL SULFONES .28. 7-RING ANNULATION - A LINCH-PIN APPROACH TO A TETRACYCLIC PRECURSOR OF THE LATHRANE DITERPENES
SYNTHESES VIA VINYL SULFONES .28. 7-RING ANNULATION - A LINCH-PIN APPROACH TO A TETRACYCLIC PRECURSOR OF THE LATHRANE DITERPENES
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DOI：
10.1021/jo00251a001
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发表时间：
1988-08-05
影响因子：
3.6
通讯作者：
FUCHS, PL
中科院分区：
文献类型：
--
作者：
BRAISH, TF;SADDLER, JC;FUCHS, PL
报道了一种手性四环中间体(5b)的合成方法。关键步骤是在没有HMPA的情况下将手性硫缩醛47加成到手性乙烯基砜40上。进一步精制得到的中间体59提供了烯醇醚67，该烯醇醚67与二甲基硫代四氟硼酸二甲酯环合得到四环中间体5b。
The synthesis of a chiral tetracyclic intermediate (5b) as a precursor of the latherane diterpenes is described. The key step is the addition of chiral thioacetal 47 to a chiral vinyl sulfone 40 in the absence of HMPA. Further elaboration of the resulting intermediate 59 provided enol ether 67, which was cyclized with dimethyl(methylthio)sufonium tetrafluoroborate to give the tetracyclic intermediate 5b.