Total synthesis of taxane terpenes: cyclase phase.

Total synthesis of taxane terpenes: cyclase phase.
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DOI:
10.1016/j.tet.2013.04.028
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发表时间:
2013-07-08
期刊:
影响因子:
2.1
通讯作者:
Baran, Phil S.
Baran, Phil S.
中科院分区:
化学3区
文献类型:
--
作者:
Ishihara, Yoshihiro;Mendoza, Abraham;Baran, Phil S.

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对低氧化紫杉烷框架的合成努力进行了全面的说明。合成了一种非天然的紫杉烷,称为“taxadienone”,这是我们在二萜中首次进入紫杉烷家族。最后的合成序列说明了该三环化合物的七步,克级和对映选择性路线,总收率为18%。然后该产物被进一步修饰得到(+)-杉二烯,这是天然产物中紫杉烷家族中氧化程度最低的成员。
A full account of synthetic efforts toward a lowly oxidized taxane framework is presented. A non-natural taxane, dubbed “taxadienone”, was synthesized as our first entry into the taxane family of diterpenes. The final synthetic sequence illustrates a seven-step, gram-scale and enantioselective route to this tricyclic compound in 18% overall yield. This product was then modified further to give (+)-taxadiene, the lowest oxidized member of the taxane family of natural products.
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