Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif

A concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid‐type pyranonaphthoquinone‐class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with...

Full description

Saved in:
Bibliographic Details
Main Authors: Yoshio Ando, Sota Ajima, Ken Ohmori
Format: Article
Language:English
Published: Wiley-VCH 2025-07-01
Series:ChemistryEurope
Subjects:
Online Access:https://doi.org/10.1002/ceur.202500086
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid‐type pyranonaphthoquinone‐class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with this study, the scalable total syntheses of nanaomycins A and D have been achieved. Based on extensive screening of reaction conditions and nucleophiles, a plausible reaction mechanism is proposed.
ISSN:2751-4765