Synthesis of a Core Carbon Framework of Cyanosporasides A and B

被引：17

作者：

Aburano, Daislike ^{[1
]}

Inagaki, Fuyuhiko ^{[1
]}

Tomonaga, Shoichirou ^{[1
]}

Mukai, Chisato ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

关键词：

PAUSON-KHAND REACTION; ASYMMETRIC TRANSFER HYDROGENATION; RING-OPENING REACTIONS; 2+2+1 CYCLOADDITION; THERMAL GENERATION; NEOCARZINOSTATIN; CONSTRUCTION; REARRANGEMENT; SUBSTITUTION; ALLENYNES;

D O I：

10.1021/jo901141t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 3-(2-ethynylphenyl)prop-2-ynyl benzenesulfinate with 2.5-mol % of [RhCl(CO)(2)](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 tile optically active 3-acetoxy-3a-cyclohexyloxy-3,3a-dihydrocyclopent[a]indene skeleton, the core carbon framework of cyanosporasides A and B.

引用

收藏

页码：5590 / 5594

页数：5

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