SYNTHESIS OF 3-SUBSTITUTED ISOCOUMARINS AND RELATED NATURAL PRODUCTS

Several N, N-diethyl-2-acylmethylbenzamides (6) were prepared from N, N-diethyl-2-toluamides (4), and the ketoamides (6) were easily cyclized to the corresponding 3-substituted isocoumarins (8) by heating in acetic acid or xylene. This simple procedure was applied to the synthesis of thunberginol A...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1993/06/15, Vol.41(6), pp.1188-1190
Hauptverfasser:	OHTA, Shunsaku, KAMATA, Yasuhiro, INAGAKI, Takayo, MASUDA, Yukari, YAMAMOTO, Satoshi, YAMASHITA, Masayuki, KAWASAKI, Ikuo
Format:	Artikel
Sprache:	eng
Schlagworte:	achlisocoumarin I Chemistry cyclization Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives isocoumarin lithiation Organic chemistry Preparations and properties thunberginol total synthesis
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Beschreibung
Zusammenfassung:	Several N, N-diethyl-2-acylmethylbenzamides (6) were prepared from N, N-diethyl-2-toluamides (4), and the ketoamides (6) were easily cyclized to the corresponding 3-substituted isocoumarins (8) by heating in acetic acid or xylene. This simple procedure was applied to the synthesis of thunberginol A (1), thunberginol B (2), thunberginol F (14), and a key-intermediate (8j) for achlisocoumarin I (3).
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.41.1188