TOTAL SYNTHESIS OF DL-TAZETTINE AND 6A-EPIPRETAZETTINE - A FORMAL SYNTHESIS OF DL-PRETAZETTINE - SOME OBSERVATIONS ON THE RELATIONSHIP OF 6A-EPIPRETAZETTINE AND TAZETTINE
TOTAL SYNTHESIS OF DL-TAZETTINE AND 6A-EPIPRETAZETTINE - A FORMAL SYNTHESIS OF DL-PRETAZETTINE - SOME OBSERVATIONS ON THE RELATIONSHIP OF 6A-EPIPRETAZETTINE AND TAZETTINE
复制标题
DOI：
10.1021/ja00390a034
复制
发表时间：
1982-01-01
影响因子：
15
通讯作者：
GAMMILL, R
中科院分区：
文献类型：
--
作者：
DANISHEFSKY, S;MORRIS, J;GAMMILL, R
亲二烯分子与二烯的Diels-Alder环加成反应生成受保护的4-芳基-4-酰基环己二烯酮。这将分两步转化为氧化的介膜衍生物。通过在甲酸氧化水平上使用原甲酸三甲酯作为C1插入剂，乙醇被转化为6a-表普他西汀O-甲醚，然后再转化为6a-表普雷他西汀。后者分4步转化为dl-tazettin。
Diels-Alder cycloaddition of dienophile with diene produces the protected 4-aryl-4-acylcyclohexadienone. This is converted in 2 steps to the oxidized mesembrine derivative. Through the novel use of trimethyl orthoformate as a C1 interpolating agent at the formic acid level of oxidation, alcohol is converted to 6a-epipretazettine O-methyl ether and then to 6a-epipretazettine. The latter is transformed in 4 steps to dl-tazettine.