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五环核心结构的构建及（）-雷尼霉素 T的形式全合成。

Construction of the Pentacyclic Core and Formal Total Synthesis of ()-Renieramycin T.

作者信息

Kimura Shinya, Saito Naoki

机构信息

Graduate School of Pharmaceutical Sciences Meiji Pharmaceutical University 2-522-1 Noshio, Kiyose Tokyo 204-8588 Japan.

出版信息

ChemistryOpen. 2018 Aug 7;7(10):764-771. doi: 10.1002/open.201800112. eCollection 2018 Oct.

DOI:10.1002/open.201800112
PMID:30338201
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6173372/
Abstract

A formal total synthesis of the antitumor marine natural product ()-renieramycin T, which possesses a characteristic ecteinascidin-type A ring in the renieramycin-saframycin core skeleton, was elaborated. The key steps in the synthesis of ()-renieramycin T are a modified Pictet-Spengler cyclization of dialkylated oxomalonate derivatives and decarboxylation via a monocarboxylic acid derivative followed by stereocontrolled protonation of the enol intermediate. A key intermediate in our previous synthesis of renieramycin T was used, and the formal synthesis was accomplished in 21 steps from a known piperazine-2,5-dione derivative.

摘要

已详细阐述了抗肿瘤海洋天然产物（）-雷尼霉素 T的形式全合成，该产物在雷尼霉素-沙弗拉霉素核心骨架中具有特征性的埃克替尼型A环。（）-雷尼霉素 T合成中的关键步骤是二烷基化草酰乙酸酯衍生物的改良Pictet-Spengler环化反应，以及通过单羧酸衍生物进行脱羧反应，随后对烯醇中间体进行立体控制质子化。使用了我们之前合成雷尼霉素 T中的关键中间体，该形式全合成从已知的哌嗪-2,5-二酮衍生物开始，经21步完成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/1dd655aae4ad/OPEN-7-764-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/8ed847244cae/OPEN-7-764-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/5b1f4839269f/OPEN-7-764-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/ffef33a490be/OPEN-7-764-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/19b32e3f7e5e/OPEN-7-764-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/8945a2438f1b/OPEN-7-764-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/1dd655aae4ad/OPEN-7-764-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/8ed847244cae/OPEN-7-764-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/5b1f4839269f/OPEN-7-764-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/ffef33a490be/OPEN-7-764-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/19b32e3f7e5e/OPEN-7-764-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/8945a2438f1b/OPEN-7-764-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/71dc/6173372/1dd655aae4ad/OPEN-7-764-g006.jpg

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