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Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-11-19 , DOI: 10.1021/acs.joc.1c01760 Naoki Kanoh 1, 2 , Yuta Terajima 3 , Suguru Tanaka 3 , Ryusei Terashima 3 , Hiromichi Nishiyama 3 , Shota Nagasawa 3 , Yusuke Sasano 3 , Yoshiharu Iwabuchi 3 , Shinichi Nishimura 4 , Hideaki Kakeya 5
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-11-19 , DOI: 10.1021/acs.joc.1c01760 Naoki Kanoh 1, 2 , Yuta Terajima 3 , Suguru Tanaka 3 , Ryusei Terashima 3 , Hiromichi Nishiyama 3 , Shota Nagasawa 3 , Yusuke Sasano 3 , Yoshiharu Iwabuchi 3 , Shinichi Nishimura 4 , Hideaki Kakeya 5
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A highly modular synthetic strategy for the heronamide C-type polyene macrolactams was established by synthesizing 8-deoxyheronamide C (2). The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named “heronamidoids” (5–8). Conformational and reactivity analysis of the heronamidoids clarified that (1) the C19 stereochemistry mainly affected the conformation of the amide linkage, resulting in the change of alignment of two polyene units and reactivity toward photochemical [6π + 6π] cycloaddition, and (2) the C8,C9-diol moiety is important for the conversion to the heronamide A-type skeleton from the heronamide C skeleton.
中文翻译：
迈向诱导多能小 (iPS) 分子的创建：Heronamide C 型多烯大环内酰胺的模块化合成策略的建立及其构象和反应性分析
通过合成 8-deoxyheronamide C ( 2 )建立了一种高度模块化的 Heronamide C 型多烯大环内酰胺合成策略。所开发的策略不仅能够实现 8-脱氧海洛因酰胺 C (2) 的全合成，而且能够统一合成四种名为“heronamidoids”的类海洛因酰胺分子 ( 5-8 )。Heronamidoids 的构象和反应性分析阐明：（1）C19 立体化学主要影响酰胺键的构象，导致两个多烯单元的排列发生变化和对光化学 [6π + 6π] 环加成的反应性，以及（2） C8，C9-二醇部分对于从heronamide C骨架转化为heronamide A型骨架很重要。
更新日期：2021-12-03
中文翻译：
迈向诱导多能小 (iPS) 分子的创建：Heronamide C 型多烯大环内酰胺的模块化合成策略的建立及其构象和反应性分析
通过合成 8-deoxyheronamide C ( 2 )建立了一种高度模块化的 Heronamide C 型多烯大环内酰胺合成策略。所开发的策略不仅能够实现 8-脱氧海洛因酰胺 C (2) 的全合成，而且能够统一合成四种名为“heronamidoids”的类海洛因酰胺分子 ( 5-8 )。Heronamidoids 的构象和反应性分析阐明：（1）C19 立体化学主要影响酰胺键的构象，导致两个多烯单元的排列发生变化和对光化学 [6π + 6π] 环加成的反应性，以及（2） C8，C9-二醇部分对于从heronamide C骨架转化为heronamide A型骨架很重要。
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