Use of the Oxazole—Olefin Diels—Alder Reaction in the Total Synthesis of the Monoterpene Alkaloids (-)-Plectrodorine and (+)-Oxerine

Autor:	Emi Shimizu, Rie Izuta, Masashi Ohba
Rok vydání:	2006
Předmět:	chemistry.chemical_compound Olefin fiber chemistry Stereochemistry Intramolecular force Monoterpene Absolute configuration Total synthesis Specific rotation General Medicine Oxazole Diels–Alder reaction
Zdroj:	ChemInform. 37
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200631181
Popis:	A full account of the total synthesis of two monoterpene alkaloids, (-)-plectrodorine [(-)-1] and (+)-oxerine [(+)-3], is presented. The key steps involved are the formation of the oxazole alcohol 10 from the gamma-butyrolactone 9 and the intramolecular Diels-Alder reaction of the oxazole-olefins 13a, b. Since the sign of specific rotation for the synthetic (+)-3 was different from that reported for natural oxerine, the absolute configuration of this alkaloid is not yet fully understood.
Databáze:	OpenAIRE
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