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Synthesis of a core carbon framework of cyanosporasides A and B.

作者信息

Aburano Daisuke, Inagaki Fuyuhiko, Tomonaga Shoichirou, Mukai Chisato

机构信息

Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

出版信息

J Org Chem. 2009 Aug 7;74(15):5590-4. doi: 10.1021/jo901141t.

DOI:10.1021/jo901141t
PMID:19558182
Abstract

Treatment of 3-(2-ethynylphenyl)prop-2-ynyl benzenesulfinate with 2.5 mol % of RhCl(CO)(2) at 40 degrees C under an atmosphere of CO effected the successive 2,3-sigmatropic rearrangement and carbonylative [2 + 2 + 1] ring-closing reaction to afford the 8-(phenylsulfonyl)-1H-cyclopent[a]-inden-2-one in a high yield. Chemical modification of the ring-closed product via lipase-mediated optical resolution produced the optically active 3-acetoxy-3a-cyclohexyloxy-3,3a-dihydrocyclopent-[a]indene skeleton, the core carbon framework of cyanosporasides A and B.

摘要

相似文献

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Rh(I)-catalyzed intramolecular [2 + 2 + 1] cycloaddition of allenenes: Construction of bicyclo[4.3.0]nonenones with an angular methyl group and tricyclo[6.4.0.0]dodecenone.
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Beilstein J Org Chem. 2011 Apr 7;7:404-9. doi: 10.3762/bjoc.7.52.