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

*E-mail: ohba.kiyomi@mf.mt-pharma.co.jp.

 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.

 http://pubs.acs.org/doi/full/10.1021/acs.orglett.5b00983

 

 

 

 

 

 

 


 

 

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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 Tang^a 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.