| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Outline of Final Research Achievements |
Eight-membered nitrogenous heterocycles (azocines) can be found in numerous naturally occurring products, such as manzamine alkaloids, grandilodines, and otonecines, as well as biologically active compounds, such as XIAP antagonists. Moreover, azocine derivatives have been utilized as synthetic intermediates in providing various alkaloids, such as loline and FR-900482. We successfully developed the effective transformation of O-propargylic oximes that possess a cyclobutyl group at the oxime moiety, in the presence of a Rh-catalyst, into the corresponding azocine oxide in good to excellent yields. In the present reaction, the starting oxime undergoes a 2,3-rearrangement to form N-allenylnitrone intermediate, then the formation of azarhodacycle, followed by ring expansion of the strained cyclobutyl group.
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