Total Synthesis and Stereochemical Revision of Iriomoteolide‐2a

Total syntheses of the proposed and correct structures of iriomoteolide‐2a, a cytotoxic marine macrolide natural product with an unusual 23‐membered macrolactone skeleton, have been accomplished for the first time. The synthesis of the correct structure involves an asymmetric epoxidation/diepoxide c...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2018-03, Vol.130 (14), p.3863-3867
Main Authors: Sakamoto, Keita, Hakamata, Akihiro, Tsuda, Masashi, Fuwa, Haruhiko
Format: Article
Language:English
Subjects:
Chemistry
Cytotoxicity
Epoxidation
Makrocyclen
Metathesis
Naturstoffe
Reaktionskaskaden
Strukturaufklärung
Synthesis
Tetrahydrofuran
Totalsynthese
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:Total syntheses of the proposed and correct structures of iriomoteolide‐2a, a cytotoxic marine macrolide natural product with an unusual 23‐membered macrolactone skeleton, have been accomplished for the first time. The synthesis of the correct structure involves an asymmetric epoxidation/diepoxide cyclization cascade for the construction of the bis(tetrahydrofuran) moiety, a Suzuki–Miyaura coupling for the fragment assembly, and a ring‐closing metathesis for the closure of the macrocyclic backbone. In addition, the original stereochemical assignment of iriomoteolide‐2a was revised. Absolut richtig: Iriomoteolid‐2a, ein cytotoxisches 23‐gliedriges Makrolid marinen Ursprungs, wurde erstmals durch Totalsynthese erhalten. Die Studien führten zur Revision der ursprünglich bestimmten Stereochemie sowie der Ermittlung der richtigen absoluten Konfiguration.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201800507