Total Synthesis and Determination of the Absolute Configuration of Naturally Occurring Mangromicin A, with Potent Antitrypanosomal Activity
Total Synthesis and Determination of the Absolute Configuration of Naturally Occurring Mangromicin A, with Potent Antitrypanosomal Activity
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天然存在的具有有效抗锥虫活性的红霉素 A 的全合成和绝对构型测定
DOI：
10.1021/acs.orglett.6b03512
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发表时间：
2017
期刊：
影响因子：
5.2
通讯作者：
Toshiaki Sunazuka
中科院分区：
文献类型：
--
作者：
Hirokazu Takada;Takeshi Yamada;Tomoyasu Hirose;Takuma Ishihara;Takuji Nakashima;Yoko Takahashi;Satoshi Omura;Toshiaki Sunazuka
完成了(+)-红豆素A的对映选择性全合成。红豆杉素A的四氢呋喃环由具有理想立体选择性的γ-羟基酮衍生的环氧羰基中间体通过mukaiyama型乙烯基烷基化构建，4-羟基二氢吡啶酮支架在全合成后期通过Dieckmann环化生成。（+）-红豆素A的可靠不对称合成揭示了天然红豆素A的绝对构型。
An enantioselective total synthesis of (+)-mangromicin A has been accomplished. The tetrahydrofuran ring of mangromicin A, possessing a tetrasubstituted carbon center, was constructed by Mukaiyama-type vinylogous alkylation via a cyclic oxocarbenium intermediate derived from a γ-hydroxy ketone with ideal stereoselectivity, and the 4-hydroxydihydropyrone scaffold was generated via Dieckmann cyclization at a late stage of the total synthesis. The reliable asymmetric synthesis of (+)-mangromicin A has revealed the absolute configuration of naturally occurring mangromicin A.