The Total Syntheses of Guttiferone A and 6-epi-Guttiferone A
The Total Syntheses of Guttiferone A and 6-epi-Guttiferone A
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DOI：
10.1021/ja500063a
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发表时间：
2014-03-12
影响因子：
15
通讯作者：
Plietker, Bernd
中科院分区：
文献类型：
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作者：
Horeischi, Fiene;Biber, Nicole;Plietker, Bernd
聚异戊二烯化多环酰基间苯三酚（PPAP）是一类不断增长的天然产物，具有共同的双环[3.3.1]壬三酮核心，目前由200多个成员组成。这一类别的各种天然产物中的子分类包括环外酰基的位置、核心的异戊烯化等级和核心内C-7处的相对构型。然而，约10%的报道结构在C-6处具有额外的手性中心。在这里，我们描述了一个简单的访问guttiferone A和epi-guttiferone A，其中通过构象控制实现立体选择性的完全控制，框架装饰和框架构建操作的严格分离设置了13个步骤的合成。
Polyprenylated polycyclic acylphloroglucinols (PPAP) are a constantly growing class of natural products that exhibit a common bicyclo[3.3.1]nonatrione core and consist of currently more than 200 members. A subclassification among the various natural products of this class includes the position of the exocyclic acyl group, the prenylation grade of the core, and the relative configuration at C-7 within the core. About 10% of the reported structures, however, possess an additional chiral center at C-6. Herein we describe a straightforward access to guttiferone A and epi-guttiferone A, in which full control of stereoselectivity is achieved via conformational control, and a strict separation of framework decorating from framework constructing operations sets the 13-steps synthesis.