120585-03-7Relevant academic research and scientific papers
Synthetic Radical Chemistry. Total Synthesis of (+/-)-Isoamijiol
Begley, Michael J.,Pattenden, Gerald,Robertson, Graeme M.
, p. 1085 - 1094 (2007/10/02)
A total synthesis of the dolastane diterpene (+/-)-isoamijiol (1), found in the brown seaweed Dictyota linearis, is described.The synthesis, which starts from cyclopentanone, uses just seven carbon-to-carbon bond forming reactions, four of which involve free radical intermediates.The 5,7-ring fused (azulene) portion in (1) was elaborated by an intramolecular -photocycloaddition (17)>-intermolecular reductive coupling (29)>cyclobutane fragmentation (15)>sequence, and the 6-ring in compuond (1) was annulated via intramolecular reductive coupling of the terminal acetylenic ketone intermediate (14) .Oxidation of compound (38), using catalytic selenium dioxide in the presence of t-butyl hydroperoxide, then produced (+/-)-isoamijiol which showed spectral data identical with naturally derived material.
