The Chemistry of Vicinal Tricarbonyls: Total Syntheses of Elastase Inhibitors YM-47141 and YM-47142

Autor:	Jyun‐Hung Chen, Mingde Xia, Harry H. Wasserman
Rok vydání:	2000
Předmět:	Depsipeptide chemistry.chemical_classification Chemistry Stereochemistry Carboxylic acid Organic Chemistry Elastase Biochemistry Phosphorane Catalysis Inorganic Chemistry chemistry.chemical_compound Ylide Drug Discovery Electrophile Physical and Theoretical Chemistry Oxidative cleavage Vicinal
Zdroj:	Helvetica Chimica Acta. 83:2607-2616
ISSN:	0018-019X
DOI:	10.1002/1522-2675(20000906)83:9<2607::aid-hlca2607>3.0.co;2-b
Popis:	We have completed the total syntheses of elastase inhibitors YM-47141 and YM-47142, the first natural products containing a vicinal tricarbonyl group. The work establishes the configuration at C(4) of the macrocyclic depsipeptide and demonstrates the generality of the phosphoranylidene-ylide activation and protection methodology employed earlier in syntheses of α-keto amides. Key steps involve the coupling of a carboxylic acid with a phosphorane to form a stable ylide intermediate, which contains the highly electrophilic carbonyl group in protected form. The tricarbonyl unit was unmasked at the final stage of the synthesis by oxidative cleavage of the C=P bond.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7540e824ebd9624fc1ab2853d353c8dc https://doi.org/10.1002/1522-2675(20000906)83:9<2607::aid-hlca2607>3.0.co Zobrazit plný text záznamu Plný text