Total synthesis of the cytotoxic macrocycle (+)-hitachimycin

Autor:	Amos B. Smith, Noritaka Chida, John L. Wood, Gary A. Sulikowski, Thomas A. Rano
Rok vydání:	1992
Předmět:	chemistry.chemical_classification Bicyclic molecule Stereochemistry Total synthesis General Chemistry Biochemistry Aldehyde Catalysis chemistry.chemical_compound Colloid and Surface Chemistry chemistry medicine Lactam Hitachimycin Stereoselectivity Enone medicine.drug Zincate
Zdroj:	Journal of the American Chemical Society. 114:8008-8022
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00047a008
Popis:	The first total synthesis of the antitumor antibiotic (+)-hitachimycin (a.k.a. stubomycin) (1) has been achieved in 22 steps and 1.1% overall yield. The cornerstone of the synthetic strategy was a highly stereoselective three-component coupling of (-)-5-methoxycyclopentenone (4) with a zincate derived from vinyl iodide 3a and aldehyde (-)-51
Databáze:	OpenAIRE
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