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(+)- 炭疽菌素 B-D 和刺桐碱 B 衍生物的短全合成。

Short Total Synthesis of (+)-Colletotryptins B-D and Mucronatin B Derivative.

机构信息

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi 20131, Thailand.

Division of Physical Science and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand.

出版信息

J Org Chem. 2024 Jun 21;89(12):8620-8631. doi: 10.1021/acs.joc.4c00552. Epub 2024 May 29.

Abstract

The short and first total synthesis of (+)-colletotryptins B-D, -colletotryptin A, and diastereomer of mucronatin B, which are a group of natural 3-(indol-2-yl)-3-(indol-3-yl)-1,2-propanediol (IIPDO) analogues containing two stereogenic centers at the C8' and C9' positions, isolated from endophytic fungus sp. SC1355 and , respectively, has been successfully accomplished in two and three steps with overall yields ranging from 28 to 54%. Key features of this synthesis include an innovative Bi(OTf)-catalyzed stereoselective transindolylation of ()-3,3'-di(1-indol-3-yl)propane-1,2-diol. The operational simplicity, environmentally friendly catalyst, and broad functional group tolerance of this modular strategy render it suitable for adoption in both academic and industrial settings.

摘要

(+)-colletotryptins B-D、-colletotryptin A 和 mucronatin B 的差向异构体的简短的和首次全合成,这些天然的 3-(吲哚-2-基)-3-(吲哚-3-基)-1,2-丙二醇(IIPDO)类似物在 C8'和 C9'位置包含两个手性中心,分别从内生真菌 sp. SC1355 和 中分离出来,已成功地在两步和三步中完成,总收率从 28%到 54%不等。该合成的关键特点包括创新性的 Bi(OTf)催化的立体选择性反吲哚基化()-3,3'-二(1-吲哚-3-基)丙烷-1,2-二醇。该模块化策略的操作简单、环境友好的催化剂和广泛的官能团耐受性使其适合在学术和工业环境中采用。

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