The total synthesis of coleophomones B, C, and D
The total synthesis of coleophomones B, C, and D
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DOI：
10.1021/ja0509984
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发表时间：
2005-06-22
影响因子：
15
通讯作者：
Mathison, CJN
中科院分区：
文献类型：
--
作者：
Nicolaou, KC;Montagnon, T;Mathison, CJN
鞘氨醇是天然产物家族的成员，它们都具有一些有趣和具有挑战性的结构特征，并表现出不寻常的生物活性。因此，它们构成了有吸引力的合成目标。本文报道了鞘氨醇酮B（2）、C（3）和D（4）的全合成。通过烯烃复分解反应，合成了高度紧张和拥挤的11元大环鞘氨醇衍生物B（2）和C（3）。此外，大环内的Delta（16，17）的两种必需几何异构体可以从共同的前体获得，促进了发散，从而使鞘氨醇B（2）/C（3）合成具有异常高的效率。鞘氨醇D（4）的合成证实，它是以异构体的动态混合物形式存在的，具有与其他家族成员不同的芳族取代模式。
Members of the coleophomone, family of natural products all possess several intriguing and challenging architectural features, as well as exhibit unusual biological activity. They, therefore, constitute attractive targets for synthesis. In this Article, we describe the total synthesis of coleophomones B (2), C (3), and D (4). The highly strained and congested 11 -membered macrocycle of coleophomones B (2) and C (3) was constructed using an impressive olefin metathesis reaction. Furthermore, both of the requisite geometric isomers of the Delta (16,17) within the macrocycle could be accessed from a common precursor, facilitating a divergence that lent the coleophomone B (2)/C (3) synthesis an unusually high degree of efficiency. The synthesis of coleophomone D (4) confirmed that it exists as a dynamic mixture of isomeric forms with a different aromatic substitution pattern from the other family members.