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Synthesis of (+)-Officinalic Acid

Bernhard Erb ; Laboratorium fur Organische Chemie der ETH Zurich, Universitatstrasse 16, CH-8092 Zurich, Switzerland
Hans-Jurg Borschberg ; Laboratorium fur Organische Chemie der ETH Zurich, Universitatstrasse 16, CH-8092 Zurich, Switzerland
Duilio Arigoni ; Laboratorium fur Organische Chemie der ETH Zurich, Universitatstrasse 16, CH-8092 Zurich, Switzerland

Sažetak

A new concept for the biosynthesis of officinalic acid (1), a C30-metabolitefrom the fungus Laricifomes officinalis, had led to an efficient synthesis of the racemic form of this compound. The key step involves a Diels-Alder dimerization of the readily available enone acid (±)-3, which furnishes (±)-officinalic acid in 420/0 yield. A byproduct formed in the same reaction in 10% yield has been named isoofficinalic acid and shown by spectroscopic techniques to possess structure 11.

Ključne riječi

Hrčak ID:

178052

URI

https://hrcak.srce.hr/178052

Datum izdavanja:

6.3.1986.

Posjeta: 812 *