Total Synthesis of (+)-Mupirocin H from d-Glucose

Udawant, Sandip P. ; Chakraborty, Tushar Kanti (2011) Total Synthesis of (+)-Mupirocin H from d-Glucose Journal of Organic Chemistry, 76 (15). pp. 6331-6337. ISSN 0022-3263

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Enantioselective total synthesis of mupirocin H is accomplished starting from d-glucose featuring strategic application of d-glucose derived chirality, diastereoselective Still–Barrish hydroboration, and further elaboration of carbon chain to furnish a phenyltetrazolyl sulfone intermediate, which on coupling with (2S,3S)-2-methyl-3-(triisopropylsilyloxy)butanal under Julia–Kocienski olefination conditions gave an advanced E-olefinic intermediate selectively. The E-olefin was transformed to the 4-hydroxynitrile, a prefinal substrate, which on acid-catalyzed oxidative lactonization furnished the target molecule mupirocin H in 19 steps from known compound 6 (longest linear sequence) with an overall yield of 4.96%.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:69571
Deposited On:14 Nov 2011 03:53
Last Modified:14 Nov 2011 03:53

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