Total Synthesis of (−)-Haouamine B Pentaacetate and Structural Revision of Haouamine B

The enantiocontrolled total synthesis of (−)‐haouamine B pentaacetate was accomplished via an optically active indane‐fused β‐lactam, which was prepared by a newly developed Friedel–Crafts reaction. Subsequent cleavage of the β‐lactam and an intramolecular McMurry coupling reaction provided the core...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2014-11, Vol.126 (48), p.13431-13435
Main Authors: Momoi, Yuichi, Okuyama, Kei-ichiro, Toya, Hiroki, Sugimoto, Kenji, Okano, Kentaro, Tokuyama, Hidetoshi
Format: Article
Language:English
Subjects:
Alkaloide
Aromatische Substitution
Cyclisierung
Kreuzkupplung
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:The enantiocontrolled total synthesis of (−)‐haouamine B pentaacetate was accomplished via an optically active indane‐fused β‐lactam, which was prepared by a newly developed Friedel–Crafts reaction. Subsequent cleavage of the β‐lactam and an intramolecular McMurry coupling reaction provided the core indane‐fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía. Revision: Schlüsselschritte der Totalsynthese des Pentaacetats von (−)‐Haouamin B (siehe Struktur) sind der enantiokontrollierte Aufbau eines Indan‐kondensierten Tetrahydropyridins durch diastereoselektive Mannich‐Reaktion nach Ellman sowie eine neu entwickelte milde Friedel‐Crafts‐Alkylierung. Die Synthese führte zu der von Trauner und Zubía bereits vorgeschlagenen Revision der Struktur des Naturstoffs.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201407686