1. The asymmetric total synthesis of cinbotolide: a revision of the original structure.
- Author
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Botubol JM, Durán-Peña MJ, Macías-Sánchez AJ, Hanson JR, Collado IG, and Hernández-Galán R
- Subjects
- Magnetic Resonance Spectroscopy, Molecular Structure, Polyketides chemical synthesis, Stereoisomerism, 4-Butyrolactone chemistry, Macrolides chemistry, Polyketides chemistry
- Abstract
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.
- Published
- 2014
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