Construction of trans-2,6-Disubstituted Piperidine Skeleton and Its Application to the Total Synthesis of (−)-Myrtine and trans-Piperidine-Type Poison-Frog Alkaloids
Takuya Okada, Kenta Eguchi, Fumiaki Hasegawa, Mir Mohd Ikhlaq, Takahiro Yoshikawa, Naoki Toyooka
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Abstract
We have succeeded in constructing a trans-2,6-disubstituted piperidine (trans-2,6-DP) skeleton by treatment of allylsilane derivative 2 with TMSOTf. Our designed trans-2,6-DP 1 has oxygen functional groups at the 2- and 6-positions and an exo-methylene moiety at the 4-position and is expected to be applied not only to the synthesis of various natural products but also as an excellent chiral building block with pseudo-symmetry. To demonstrate the versatility of 1, the total synthesis of (−)-myrtin and trans-piperidine-type poison-frog alkaloid 213A and 213B was accomplished.
期刊介绍：
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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