Stereoselective Synthesis of the C9-C19 Fragment of Lyngbyaloside B and C via Ether Transfer.
Summary of "Stereoselective Synthesis of the C9-C19 Fragment of Lyngbyaloside B and C via Ether Transfer."
A stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C highlighted, by an extension of our ether transfer methodology, enables the formation of tertiary ethers. 2-Naphthylmethyl ethers have been shown to proceed efficiently through ether transfer with high stereoselectivity and are easily deprotected by DDQ oxidation. Variation of the workup conditions results in the stereoselective formation of syn-1,3-diol mono- or diethers.
Affiliation
Department of Chemistry and Biochemistry and the Mike and Josie Harper Cancer Research Institute, University of Notre Dame , 251 Niewland Science Hall, Notre Dame, Indiana 46556, United States.
Journal Details
This article was published in the following journal.
Name: Organic letters
ISSN: 1523-7052
Pages: 3490-3
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22716968
- DOI: http://dx.doi.org/10.1021/ol301455p
Medical and Biotech [MESH] Definitions
Rna, Transfer, Ala
A transfer RNA which is specific for carrying alanine to sites on the ribosomes in preparation for protein synthesis.
Rna, Transfer, Lys
A transfer RNA which is specific for carrying lysine to sites on the ribosomes in preparation for protein synthesis.
Rna, Transfer, Arg
A transfer RNA which is specific for carrying arginine to sites on the ribosomes in preparation for protein synthesis.
Rna, Transfer, Asn
A transfer RNA which is specific for carrying asparagine to sites on the ribosomes in preparation for protein synthesis.
Rna, Transfer, Gln
A transfer RNA which is specific for carrying glutamine to sites on the ribosomes in preparation for protein synthesis.
PubMed Articles
Efficient and stereoselective synthesis of the disaccharide fragment of incednine.
Efficient and stereoselective synthesis of a disaccharide fragment, 2-deoxy-4-O-(N'-monodemethyl-d-forosaminyl)-2-methylamino-β-d-xylopyranoside, of a novel antibiotic, incednine (1), is described. T...
Stereoselective synthesis of the C15-C26 fragment of the antitumor agent (-)-dictyostatin.
The synthesis of the C15-C26 fragment of (-)-dictyostatin is reported in 10 steps and 28% overall yield. The key steps are the two stereoselective sulfoxide-directed processes: a Reformatsky-type reac...
A stereoselective synthesis of the C9-C19 subunit of (+)-peloruside A.
The stereoselective synthesis of a C9-C19 fragment of the potent antitumor agent peloruside A is disclosed. The C11 stereogenic centre was created by a vinylogous Mukaiyama aldol reaction following Ca...
Synthesis of (±)-Acetylnorloline via Stereoselective Tethered Aminohydroxylation.
Loline alkaloids exhibit a strained ether-bridged pyrrolizidine skeleton and possess insecticidal and insect antifeedant properties. The synthesis of acetylnorloline, a prototypical member of the alka...
Stereoselective synthesis and rearrangement-fragmentation of arylidene N-alkoxydiketopiperazines.
A stereoselective synthesis of arylidene N-alkoxydiketopiperazines via oxime-ether formation and intramolecular acylation is described, followed by an acid-catalysed rearrangement-fragmentation to giv...
Clinical Trials
A Study Evaluating the Effects of Lipid Lowering Treatment on Steroid Synthesis
Cholesterol is the precursor of glucocorticoids, mineralocorticoids and sex steroids. Both adrenal and non-adrenal (ovarian + testicular) all steroid hormones are primarily synthesized usi...
Study To Evaluate Upper Arm Autologous Fat Transfer
The objective of this pilot study is to observe the utility of autologous transfer of fat collected using ultrasonic assisted liposuction into the upper arms with ultrasonic visualization.
The purpose of this study is to determine whether embryo transfer on day 3 versus day 5 shows a significant difference in implantation, clinical pregnancy, live birth, miscarriage and mult...
Embryo Transfer: Direct Versus Afterloading Trial
The purpose of this study is to evaluate two types of embryo transfer procedure. The investigators will compare direct embryo transfer against afterloading embryo transfer.
Optimal Timing For Embryo Transfer For Low Responder Patients
Women undergoing in vitro fertilization (IVF) therapy, who are low responder and agree to enter the trial will be randomized to a study group, for whom embryo transfer will be done on the...
