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The Chemistry of Vicinal Tricarbonyls: Total Syntheses of Elastase Inhibitors YM‐47141 and YM‐47142
Author(s) -
Wasserman Harry H.,
Chen JyunHung,
Xia Mingde
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000906)83:9<2607::aid-hlca2607>3.0.co;2-b
Subject(s) - chemistry , vicinal , phosphorane , electrophile , ylide , stereochemistry , nucleophile , cleavage (geology) , medicinal chemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
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.