Total Synthesis of Diospyrodin and Its Three Diastereomers

Antibacterial diospyrodin (1) was synthesized in 13 steps. Et3B and O2 promoted the formation of an α-alkoxy carbon radical from l-ribose-derived α-alkoxyacyl telluride 5, which reacted with d-glucose-derived aldehyde 4. The radical addition realized the convergent assembly of the contiguously hydro...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (16), p.6468-6472
Main Authors: Fukuda, Takumi, Nagatomo, Masanori, Inoue, Masayuki
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Antibacterial diospyrodin (1) was synthesized in 13 steps. Et3B and O2 promoted the formation of an α-alkoxy carbon radical from l-ribose-derived α-alkoxyacyl telluride 5, which reacted with d-glucose-derived aldehyde 4. The radical addition realized the convergent assembly of the contiguously hydroxylated carbon-chain of 3-α and greatly contributed to streamlining the synthetic route. Compound 3-α was transformed not only to 1 but also to its three diastereomers by functional group manipulations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02280