天然抗生素炭疽霉素的不对称全合成。
Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin.
作者信息
Davison Emma K, Freeman Jared L, Zhang Wanli, Wuest William M, Furkert Daniel P, Brimble Margaret A
机构信息
School of Chemical Sciences, University of Auckland, 23 Symonds Street, Auckland, 1010, New Zealand.
School of Biological Sciences, University of Auckland, 3 Symonds Street, Auckland, 1010, New Zealand.
出版信息
Org Lett. 2020 Jul 17;22(14):5550-5554. doi: 10.1021/acs.orglett.0c01913. Epub 2020 Jun 29.
Abstract
The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels-Alder reaction to forge the -decalin moiety, and an unprecedented aldol reaction using a complex β-ketoester to provide the tricarbonyl motif. A Stork-Zhao olefination and Grubbs ring closing metathesis delivered the /-diene and forged the macrocycle. The C2 configuration was set with a base-mediated epimerization, providing access to (-)-anthracimycin.
摘要
强效抗生素炭疽霉素的首次全合成在20步反应中完成。该合成的特点是通过分子内狄尔斯-阿尔德反应构建十氢化萘部分，并使用一种复杂的β-酮酯进行前所未有的羟醛反应以提供三羰基基序。一次斯托克-赵烯烃化反应和格拉布闭环复分解反应生成了α,β-二烯并构建了大环。通过碱介导的差向异构化确定了C2构型，从而得到(-)-炭疽霉素。
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