Enantioselective synthesis of the carbacephem antibiotic loracarbef via Mitsunobu and Dieckmann cyclization from an unnatural amino acid

Misner, Jerry W.; Fisher, Jack W.; Gardner, J; Pedersen, Steve W; Trinkle, Kristina L.; Jackson, B.; Zhang, Tony Y.

doi:10.1016/s0040-4039(03)01483-7

Cited by 23 publications

(7 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A similar intramolecular etherification afforded interesting carbocyclic nucleosides such as 252 (Scheme c); the derivative with a PMB group in place of triphenylmethyl (Trt) is also known . Oxazoline formation by this route appears to be facile, and many useful ligands for transition metals and an intermediate for norpseudoephedrine ( 253 , Scheme d) have been synthesized. , An unwanted oxazoline formation was noted by Jackson and Zhang in the course of their studies on the carbacephem antibiotic loracarbef . In the reactions of saccharins, Woodward and co-workers observed O -alkylation with alcohols using a Mitsunobu protocol, while that using alkyl halide and a base afforded N -alkylated derivatives .…”

Section: Phenols and Alcohols As Nucleophiles: Ether Formationmentioning

confidence: 98%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

View full text Add to dashboard Cite

His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

show abstract

Section: Phenols and Alcohols As Nucleophiles: Ether Formationmentioning

confidence: 98%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

View full text Add to dashboard Cite

show abstract

“…The benzyl ester moiety of all -syn - 15 was subsequently cleaved by hydrogenolysis using standard conditions (Scheme 6) [69]. The tricarboxylic acid all -syn- 16 was isolated in almost quantitative yield.…”

Section: Resultsmentioning

confidence: 99%

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

Lohoelter¹,

Brutschy²,

Lubczyk³

et al. 2013

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe readily available ex-chiral-pool building block (−)-isosteviol was combined with the C 3-symmetric platforms hexahydroxytriphenylene and hexaaminotriptycene providing large and rigid molecular architectures. Because of the persistent cavities these scaffolds are very potent supramolecular affinity materials for head space analysis by quartz crystal microbalances. The scaffolds serve in particular as templates for tracing air-borne arenes at low concentration. The affinities of the synthesized materials towards different air-borne arenes were determined by 200 MHz quartz crystal microbalances.

show abstract

“…Several examples of successful dephthaloylation in one step using hydrazine derivatives have been reported for monocyclic β-lactam, but only a few examples are described for bicyclic derivatives like cephalosporins, [39] carbacephems, [42] and isocephems. [43] As previously reported, [44] we observed that it was not possible to carry out efficient hydrazinolysis on penicillin derivatives without β-lactam ring-opening.…”

Section: Resultsmentioning

confidence: 99%