Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy to the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis

28 July 2021, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A highly modular synthetic strategy to 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 towards 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.

Keywords

Polyene Macrolactams
Total Synthesis
Heronamide C
Reactivity Analysis
Unified Synthesis
iPS Molecules

Supplementary materials

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Description
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Title
Supporting Information for Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy to the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis
Description
Structure of all reported heronamides; Cartesian coordinates (angstroms) for DFT-optimized structure of heronamidoids 𝛾 (7) and 𝛿 (8); copies of the NMR spectra of synthesized compounds (PDF).
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