The asymmetric total synthesis of cinbotolide: a revision of the original structure.
The structure 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1) was assigned to a metabolite of Botrytis cinerea, but the spectra of several synthetic analogues had significant differences from that of 1. Examination of the constituents of a B. cinerea mutant that overproduces polyketides gave sufficient quantities of 1, now named cinbotolide, for chemical transformations. These led to a revised γ-butyrolactone structure for the metabolite. This structure has been confirmed by an asymmetric total synthesis, which also established its absolute configuration.
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biomoléculas, Campus Universitario Rio San Pedro s/n, Universidad de Cádiz , 11510 Puerto Real, Cádiz, Spain.
José Manuel
JM
Botubol
María Jesús
MJ
Durán-Peña
Antonio J
AJ
Macías-Sánchez
James R
JR
Hanson
Isidro G
IG
Collado
Rosario
R
Hernández-Galán
D015107:4-Butyrolactone / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D061065:Polyketides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D018942:Macrolides; D061065:Polyketides; C000599070:cinbotolide; D015107:4-Butyrolactone