Total Synthesis of (+)-Mupirocin H from d-Glucose.
Summary of "Total Synthesis of (+)-Mupirocin H from d-Glucose."
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%.
Affiliation
CSIR-Indian Institute of Chemical Technology , Hyderabad 500607, India.
Journal Details
This article was published in the following journal.
Name: The Journal of organic chemistry
ISSN: 1520-6904
Pages: 6331-7
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/21707103
- DOI: http://dx.doi.org/10.1021/jo200396q
Medical and Biotech [MESH] Definitions
Glucose Clamp Technique
Maintenance of a constant blood glucose level by perfusion or infusion with glucose or insulin. It is used for the study of metabolic rates (e.g., in glucose, lipid, amino acid metabolism) at constant glucose concentration.
Glucose Transporter Type 2
A glucose transport facilitator that is expressed primarily in PANCREATIC BETA CELLS; LIVER; and KIDNEYS. It may function as a GLUCOSE sensor to regulate INSULIN release and glucose HOMEOSTASIS.
Glucose-6-phosphatase
An enzyme that catalyzes the conversion of D-glucose 6-phosphate and water to D-glucose and orthophosphate. EC 3.1.3.9.
Glucose Tolerance Test
A test to determine the ability of an individual to maintain HOMEOSTASIS of BLOOD GLUCOSE. It includes measuring blood glucose levels in a fasting state, and at prescribed intervals before and after oral glucose intake (75 or 100 g) or intravenous infusion (0.5 g/kg).
Glucose Transporter Type 1
A ubiquitously expressed glucose transporter that is important for constitutive, basal GLUCOSE transport. It is predominately expressed in ENDOTHELIAL CELLS and ERYTHROCYTES at the BLOOD-BRAIN BARRIER and is responsible for GLUCOSE entry into the BRAIN.
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