Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin

The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclizati...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1991/11/25, Vol.39(11), pp.3048-3050
Hauptverfasser:	TAKEUCHI, Yasuo, WATANABE, Ikuo, TOMOZANE, Hideo, HASHIGAKI, Kuniko, YAMATO, Masatoshi
Format:	Artikel
Sprache:	eng
Schlagworte:	chelation control Chemistry diastereoselective Michael reaction dl-griseofulvin Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties reaction mechanism
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Zusammenfassung:	The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.39.3048