Abstract
This paper presents a brief review on the history of the development of Ni(II)/Cr(II)-mediated coupling reaction and its application to natural products syntheses. During the synthetic studies on the marine natural product palytoxin, we recognized the trans-allylic benzylether benzoate to be the key intermediate for the synthesis of the C.8-C.22 segment (ref. 1-4). We had planned to synthesize this substance from the aldehyde or its synthetic equivalent, which seemed possible through routine synthetic operations. However, we soon realized that standard synthetic routes such as Wittig and aldol approaches were not as practical as we had hoped. reaction utilizing organocuprates gave, at least in the model series, very promising results. However, in spite of extensive efforts, we were unable to generate the desired organocuprate reagent from the trans-iodoolefin , Among the many possibilities attempted, a coupling
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