期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 130, 期 6, 页码 2087-2100出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja076663z
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资金
- NCI NIH HHS [1 R01 CA/GM93591-01A] Funding Source: Medline
An efficient and highly stereoselective total synthesis of the natural product (+/-)-welwitindolinone A isonitrile (1) is described. The bicyclo[4.2.0]octane core of 1 was established by a regio- and diastereoselective [2+2] ketene cycloaddition. The C12 quaternary center and vicinal stereogenic chlorine were installed in a single operation with excellent stereocontrol via a chloronium ion mediated semipinacol rearrangement. Described strategies for construction of the spiro-oxinole include a SMl(2)-LiCl mediated reductive cyclization and a novel anionic cyclization that simultaneously constructs the spiro-oxindole and vinyl isonitrile moieties.
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