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The streochemical, course of the 1,5-shift of hydrogen in the biosynthesis of ophiobolins

✍ Scribed by L. Canonica; A. Fiecchi; H.Galli Kienle; B.M. Ranzi; A. Scala


Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
123 KB
Volume
8
Category
Article
ISSN
0040-4039

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πŸ“œ SIMILAR VOLUMES


The biosynthesis-of ophiobolins
✍ L. Canonica; A. Fiecchi; M.Galli Kienle; B.M. Ranzi; A. Scala; T. Salvatori; E. πŸ“‚ Article πŸ“… 1967 πŸ› Elsevier Science 🌐 French βš– 314 KB

Ophiobolins A and B (1) are substances constructed from five isoprene units linearly linked head to tail (2). In their biogenetic hypothesis Nozoe et al. proposed that the introduction of a 3-hydroxyl substituent is accounted for by attack at 3-C by an agent which transfers OH+ (3).

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## Abstract 7‐Phenylcycloheptatriene‐1,3,5 rearranges on heating to a mixture of the 3‐, 1‐ and 2‐isomers. These are formed in the order indicated by successive trans‐annular 1‐5 shifts of hydrogen. The isomerization of the 7‐ to the 3‐isomer, by which the trienic and aromatic systems enter into co