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

Udawant, S P; Chakraborty, Tushar Kanti

dc.contributor.author	Udawant, S P
dc.contributor.author	Chakraborty, Tushar Kanti
dc.date.accessioned	2011-10-05T10:26:15Z
dc.date.available	2011-10-05T10:26:15Z
dc.date.issued	2011
dc.identifier.citation	J. Org. Chem., (2011), 76 (15), 6331–6337	en
dc.identifier.uri	http://hdl.handle.net/123456789/733
dc.description.abstract	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 pre-final 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%.	en
dc.format.extent	533226 bytes
dc.format.mimetype	application/pdf
dc.language.iso	en	en
dc.relation.ispartofseries	cdricommunicationno.8089	en
dc.subject	D-glucose	en
dc.subject	4-hydroxynitrile	en
dc.subject	E-olefin	en
dc.subject	molecule mupirocin H	en
dc.title	Total Synthesis of (+)-Mupirocin H from D-Glucose	en
dc.type	Article	en