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

Naoki Kanoh, Yuta Terajima, Suguru Tanaka, Ryusei Terashima, Hiromichi Nishiyama, Shota Nagasawa, Yusuke Sasano, Yoshiharu Iwabuchi, Shinichi Nishimura, Hideaki Kakeya

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1 Citation (Scopus)

Abstract

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.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2021

ASJC Scopus subject areas

  • Organic Chemistry

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