期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 71, 期 23, 页码 8982-8985出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo061588g
关键词
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A series of polyyne natural products 1, 13, and 31 and analogues 14, 21, and 22 are synthesized in six steps. The key step is a Fritsch-Buttenberg-Wiechell rearrangement in which a triyne framework is formed from the appropriate dibromoolefin precursor. Terminal conjugated triynes 13 and 14 are obtained as highly unstable products that rapidly decompose under ambient conditions. The stability of triynols increases via either the addition of methylene units (i.e., 6 -> 31 -> 1) or addition of terminal substituents (i.e., 13 -> 21 or 31).
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