ハプロフィチンの全合成研究

抄録

Haplophytine is the major alkaloid isolated from the dried leaves of the Mexican plant Haplophyton cimicidum, and exhibits an insecticidal activity. In spite of its unique and interesting structure that would attract strong interest of synthetic chemists, no total synthesis of haplophytine has been reported even after five decades from its isolation. We report herein the model studies for the construction of the left-hand segment of haplophytine, containing the unique bicyclo[3.3.1]skeleton, by biomimetic skeletal rearrangement. Furthermore, we have synthesized the optically active tetrahydro-β-carboline derivative, a key intermediate for the synthesis of the left hand segment, utilizing tin-mediated indole synthesis developed in our laboratory.

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