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Total synthesis of (-)-cassine
Hidefumi Makabe1, Looi Kok Kong, Mitsuru Hirota
1Graduate School of Agriculture, Sciences of Functional Foods, Shinshu University, 8304 Minami-minowa Kami-ina, Nagano 399-4598, Japan. makabeh@gipmc.shinshu-u.ac.jp
Organic Letters
|January 3, 2003
Summary
Palladium chloride (PdCl2) catalyzed cyclization of amino allylic alcohol yields a key intermediate with high diastereoselectivity. This intermediate is versatile for synthesizing piperidine alkaloids, as shown by the total synthesis of (-)-cassine.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Chemistry
Background:
- Piperidine alkaloids are a significant class of natural products with diverse biological activities.
- Developing efficient synthetic routes to complex piperidine structures remains a challenge in organic synthesis.
Purpose of the Study:
- To develop a diastereoselective synthesis of cis-2,6-disubstituted piperidine precursors.
- To demonstrate the utility of the synthesized intermediate in natural product synthesis.
Main Methods:
- Palladium(II) chloride (PdCl2)-catalyzed cyclization of an amino allylic alcohol.
- Total synthesis of (-)-cassine utilizing the cyclized product as a building block.
Main Results:
- The PdCl2-catalyzed cyclization proceeded with excellent diastereoselectivity, affording the desired cyclized product (17a).
- Compound 17a proved to be a versatile synthon for constructing the piperidine core.
- The total synthesis of (-)-cassine (1) was successfully achieved, validating the synthetic strategy.
Conclusions:
- The PdCl2-catalyzed cyclization offers a highly diastereoselective route to valuable piperidine building blocks.
- The developed methodology provides an efficient pathway for the synthesis of complex piperidine alkaloids like (-)-cassine.