期刊
NATURE PROTOCOLS
卷 8, 期 3, 页码 501-508出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/nprot.2013.017
关键词
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资金
- US National Institutes of Health [GM65597, CA76497]
- University of Minnesota Graduate School Doctoral Dissertation Fellowship
- National Science Foundation
The hexadehydro-Diels-Alder (HDDA) cascade enables the synthesis of complex benzenoid products with various substitution patterns through aryne intermediates. The first stage of this cascade involves the generation of a highly reactive ortho-benzyne intermediate by a net [4 + 2] cycloisomerization of a triyne substrate. The benzyne can be rapidly 'trapped' either intramolecularly or intermolecularly with myriad nucleophilic or pi-bond-donating reactants. As a representative example of a general procedure for synthesizing highly substituted benzenoids, this protocol describes the synthesis of a typical triyne substrate and its use as the reactant in an HDDA cascade to form a phthalide. The synthetic procedure detailed herein (four chemical reactions) takes 16-20 h of active effort over a period of several days for the preparation of the triyne precursor and similar to 2 h of active effort over a 3-d period for the generation and trapping of the benzyne and isolation of the phthalide product.
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