Synthesis and stability of a homologous series of triynol natural products and their analogues.
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).
Luu
Thanh
T
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Tykwinski
Rik R
RR
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000480:Alkynes; D001685:Biological Factors