Total Synthesis of Brazilin
Total Synthesis of Brazilin
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DOI：
10.1021/jo502745j
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发表时间：
2015-02-06
影响因子：
3.6
通讯作者：
Kim, Ikyon
中科院分区：
文献类型：
--
作者：
Jung, Youngeun;Kim, Ikyon
本文描述了一种从市售起始原料经9步高效全合成巴西林的方法，总收率为70%。Mitsunobu耦合，然后在（III）催化的炔醛复分解允许快速建设巴西林核心骨架定量产量。随后的氧化水平和酸催化环化的调制导致巴西林的三甲基醚。还证明了关键中间体的不对称二羟基化，这将允许不对称获得（+）-brazilin。
Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.