Synthetics and structural studies on novel gibberellins

Autor:	Jonathan C. Morris, G. R. King, M. Pour, N. J. T. Monck, Lewis N. Mander, Hongbin Zhang
Rok vydání:	1998
Předmět:	Cyclopropanation Stereochemistry Chemistry General Chemical Engineering food and beverages Total synthesis General Chemistry Ring (chemistry) Cycloaddition chemistry.chemical_compound Intramolecular force Organic chemistry Gibberellin Tetralin
Zdroj:	Pure and Applied Chemistry. 70:351-354
ISSN:	1365-3075 0033-4545
DOI:	10.1351/pac199870020351
Popis:	The structure elucidation of a number of metabolites isolated during biosynthetic studies on gibberellin-like fern antheridiogens from the Anemia genus has been undertaken by synthesising a series of reference samples from gibberellin A7. Two of the metabolites were shown to be the 12p- and 12a-hydroxy derivatives of 9~,15-cyclogibberellin A9 (1) while the 1 lp-hydroxy isomer was identical with a new gibberellin (GAlog) from developing apple seeds. In a cognate study, an efficient total synthesis of this type of gibberellin has baen developed, the key step being the intramolecular cyclopropanation reactions of the aromatic ring in tetralin 2-diazomethyl ketones to give stable norcaradiene products. The (4+2) cycloaddition of selected dienophiles to some of these products allows the rapid stereo-controlled assembly of (1) and related gibberellins.
Databáze:	OpenAIRE
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