Efficient syntheses of pterulone, pterulone B and related analogues.
An efficient synthesis of the three halogenated naturally occurring products, pterulone (2), pterulone B (3) and alcohol 5, and of a wide range of related unnatural analogues has been achieved starting from the two readily available 1-benzoxepine sulfonyl-containing intermediates 6a and 6b. The biological activities of pterulone and some of the synthesized analogues were tested against a wide spectrum of phytopathogenic fungi.
Lemaire
Philippe
P
Laboratoire de Chimie Organique 1, CNRS UMR 5622, Université Claude Bernard, Lyon I, CPE. 43, Bd du 11 Novembre 1918, 69622 Villeurbanne, France.
Balme
Geneviève
G
Desbordes
Philippe
P
Vors
Jean-Pierre
JP
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry / Q000187:drug effects; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019800:Phenol / Q000737:chemistry; D013329:Structure-Activity Relationship
D000438:Alcohols; D000935:Antifungal Agents; D001572:Benzofurans; D010082:Oxepins; C106752:pterulone; D019800:Phenol