A synthetic approach to 5/5/6-polycyclic tetramate macrolactams of the discodermide type

A flexible synthetic route to the 16-membered tetramate-embedding macrocyclic scaffold present in various polycyclic tetramate macrolactams (PTMs) was developed which differs from the seminal synthesis of ikarugamycin by Boeckman Jr. in protecting groups and the order of connections. We also devised...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2022-01, Vol.104, p.132113, Article 132113
Main Authors: Bodenschatz, Kevin, Stöckl, Julia, Winterer, Markus, Schobert, Rainer
Format: Article
Language:English
Subjects:
Discodermide
Polycyclic tetramate macrolactams
Weiss diketone
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:A flexible synthetic route to the 16-membered tetramate-embedding macrocyclic scaffold present in various polycyclic tetramate macrolactams (PTMs) was developed which differs from the seminal synthesis of ikarugamycin by Boeckman Jr. in protecting groups and the order of connections. We also devised a short approach to various stereoisomers of the 5/5/6-tricarbocyclic motif found in discodermide and other PTMs, starting from the Weiss’ diketone. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.132113