Polyene cyclization promoted by the cross-conjugated α-carbalkoxy enone system.: Observation on a putative 1,5-hydride/1,3-alkyl shift under Lewis acid catalysis

被引：17

作者：

Chou, Ho-Hsuan ^{[2
]}

Wu, Huang-Min ^{[2
]}

Wu, Jen-Dar ^{[2
]}

Ly, Tai Wei ^{[3
]}

Jan, Ning-Wei ^{[2
]}

Shia, Kak-Shan ^{[1
]}

Liu, Hsing-Jang ^{[2
]}

机构：

[1] Natl Hlth Res Inst, Div Biotechnol & Pharmaceut Res, Taipei 350, Miaoli County, Taiwan

[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

[3] Actimis Pharmaceut Inc, San Diego, CA 92121 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 01期

关键词：

D O I：

10.1021/ol702631q

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Polyene cyclization of compounds 3 and 4 under catalysis with AlCl3 and/or SnCl4 gave rise to complex bicyclic products 8 and 9, structures of which were highly unexpected, and X-ray analyses were invoked for unambiguously structural identification. Mechanistically, a tandem or-bond rearrangement process, including an unusual through-space 1,5-hydride or 1,3-alkyl shift as a key operation, is proposed.

引用

页码：121 / 123

页数：3

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