Asymmetric Total Synthesis of the 1- e pi -Aglycon of the Cripowellins A and B - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2005

Asymmetric Total Synthesis of the 1- e pi -Aglycon of the Cripowellins A and B

Résumé

The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epi-aglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee ≥ 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

Domaines

Chimie organique
Fichier principal
Vignette du fichier
J. Org. Chem. 2005, 70, 10538-10551 Cripo.pdf (739.71 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)

Dates et versions

hal-02371135 , version 1 (08-10-2021)

Identifiants

Citer

Dieter Enders, Achim Lenzen, Michael Backes, Carsten Janeck, Kelly Catlin, et al.. Asymmetric Total Synthesis of the 1- e pi -Aglycon of the Cripowellins A and B. Journal of Organic Chemistry, 2005, 70 (25), pp.10538-10551. ⟨10.1021/jo0518093⟩. ⟨hal-02371135⟩

Collections

CNRS UP-SANTE
85 Consultations
43 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More