Asian Journal of Organic Chemistry
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Managing Editor: Richard Threlfall; Editorial Board Chairs: Sung Ho Kang, Keiji Maruoka, Deqing Zhang
Impact Factor: 2.292
ISI Journal Citation Reports © Ranking: 2013: 27/58 (Chemistry Organic)
Online ISSN: 2193-5815
August 01, 2014
VIP: Synthesis of 19-Nor-Vitamin D A-Ring Synthons via Ring-Closing Olefin Metathesis
Yu Nagai, Tomoe Tanami, Junko Abe, Dr. Hazuki Nagai, Toru Hamamizu, Kaichiro Kominato, Keisuke Iida and Prof. Dr. Kazuo Nagasawa
Give me a D: A synthetic method for making A-ring synthons for 19-nor-vitamin D was developed based on ring-closing olefin metathesis (RCM) with a linear precursor, followed by palladium-catalyzed isomerization of the endocyclic olefin product to give the target exocyclic olefin. PG=protecting group; TBS=tert-butyldimethylsilyl; Tf=trifluoromethanesulfonyl.
Recently Published Articles
- Phosphotungstic Acid as an Efficient Catalyst for Allylation of Isatins and N-tert-Butyloxycarbonylamido Sulfones Under Solvent-Free Conditions
Debashis Ghosh , S. Saravanan, Naveen Gupta, Sayed H. R. Abdi, Noor-ul H. Khan, Rukhsana I. Kureshy and Hari C. Bajaj
Article first published online: 12 SEP 2014 | DOI: 10.1002/ajoc.201402130
Allyl in style: The present work discloses the highly efficient allylation of isatin derivatives as well as N-tert-butyloxycarbonylamido sulfones using phosphotungstic acid as the catalyst under ambient and solvent-free reaction conditions. The allylation products N-tert-butyloxycarbonyl (Boc) homoallyl amines were successfully epoxidized to get the corresponding epoxides in very good yields.
- Isolation and Characterization of 1 β-Acetoxypolygodial from Tasmannia lanceolata
Ross M. Deans, Michael G. Gardiner, James Horne, Amos C. Hung, Christopher J. T. Hyland, Jeremy Just, Jason A. Smith and JieXiang Yin
Article first published online: 9 SEP 2014 | DOI: 10.1002/ajoc.201402105
New from old: A natural product not previously reported has been isolated from Tasmannia lanceolata. This compound is related to the previously reported polygodial, but features an acetoxy group at the C1 position.
- Tandem Synthesis of Polysubstituted Pyridines via the Indium(III)-Triflate-Catalyzed Cycloaddition/Oxidative Aromatization of Blaise Reaction Intermediates with α,β-Unsaturated Ketones
Zi Xuan, Dr. Kris Rathwell and Prof. Dr. Sang-gi Lee
Article first published online: 9 SEP 2014 | DOI: 10.1002/ajoc.201402122
Three Sum to Six: A tandem, one-pot method for the synthesis of polysubstituted pyridines with complete control of the substitution pattern has been developed. Zinc bromide β-enamino esters from the Blaise reaction of nitriles with a Reformatsky reagent undergo Michael addition with conjugated ketones catalyzed by In(OTf)3. Final intramolecular cyclization and oxidative aromatization yields polysubstituted pyridines. Tf=trifluoromethanesulfonyl.
- Continuous Flow and Microwave-Assisted Vorbrüggen Glycosylations: Historical Perspective to High-Throughput Strategies
Dr. Atul Manvar and Prof. Anamik Shah
Article first published online: 4 SEP 2014 | DOI: 10.1002/ajoc.201402119
Historical to high-throughput: One of the most frequently used methods for glycosylation, the silyl Hilbert–Johnson reaction, or Vorbrüggen glycosylation, is summarized from the point of view of high-throughput microwave- and continuous-flow-assisted superheating. Especially, continuous-flow methods unlock an opportunity for developing synthetic processes through miniaturization.
- Copper-Free Sonogashira Coupling Reaction Catalyzed by PVC-Supported Triazine Palladium(II) Complex Under Aerobic Conditions
Mohammad Bakherad, Ali Keivanloo, Amene Hadi and Maesoume Siavoshi
Article first published online: 3 SEP 2014 | DOI: 10.1002/ajoc.201402125
Easy as PVC: A PVC-supported triazine palladium(II) complex is a highly active catalyst for the copper-free Sonogashira coupling of aryl halides with terminal alkynes at room temperature under aerobic conditions. This phosphine-free heterogeneous palladium catalyst can be easily recovered from the products and reused many times. DMF=N,N-dimethylformamide.