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Sunday, 19 July 2015

Paecilomycin B


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天然物有機化学研究室 の最近の論文目録で す

● Kiyomi Ohba and Masaya Nakata
"Total Synthesis of Paecilomycin B"
Kiyomi Ohba * and Masaya Nakata
Medicinal Chemistry Research Laboratories, Mitsubishi Tanabe Pharma Corporation, 1000 Kamoshida-cho, Aoba-ku, Yokohama 227-0033, Japan
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Org. Lett., 2015, 17 (12), pp 2890–2893
DOI: 10.1021/acs.orglett.5b00983
Publication Date (Web): May 4, 2015
 Starting from the glucose-derived δ-lactone and the functionalized aryl bromide, the first total synthesis of naturally occurring paecilomycin B was achieved via functionalized aryl-β-C-glycoside synthesis using 2,4,6-triisopropylphenyllithium under Barbier-type reaction conditions and ring-closing metathesis as the key steps.
 
 
 
 
 
 
 


 

 

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Tuesday, 12 May 2015

Zinc diiodide-promoted synthesis of trisubstituted allenes from propargylic amines

Org. Chem. Front., 2015, 2,470-475
DOI: 10.1039/C5QO00047E, Research Article
Jinqiang Kuang, Xinjun Tang, Shengming Ma
Zinc diiodide has been identified as an effective reagent for the efficient synthesis of trisubstituted allenes from propargylic amines.



Jinqiang Kuang,a   Xinjun Tanga and   Shengming Ma*ab  

a
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: masm@sioc.ac.cn
b
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. China
Org. Chem. Front., 2015,2, 470-475

DOI: 10.1039/C5QO00047E, http://pubs.rsc.org/en/Content/ArticleLanding/2015/QO/C5QO00047E#!divAbstract
Zinc diiodide has been identified as an effective reagent for the efficient synthesis of trisubstituted allenes from propargylic amines. Compared to CdI2 this protocol offers a green approach. Due to the easy preparation of propargylic amines through the method developed by this group, this method provides a two-step synthesis of trisubstituted allenes from 1-alkynes, ketones, and pyrrolidine. Finally, an efficient synthesis of such trisubstituted allenes from 1-alkynes, ketones, and pyrrolidine via simple filtration has been developed. Compared with the CdI2-mediated protocol, the current protocol enjoys a much wider scope for ketones and affords functionalized allenes without further cyclization in some substrates.