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Synthetic Study of (−)‐Norzoanthamine: Construction of the ABC Ring Moiety |
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| Authors: | Yoshihisa Murata Dr Daisuke Yamashita Katsushi Kitahara Yohei Minasako Atsuo Nakazaki Dr Susumu Kobayashi Prof?Dr |
| Institution: | Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda‐shi, Chiba 278‐8510 (Japan), Fax: (+81)?4‐7121‐3671 |
| Abstract: | Throw your hat in the ring : A highly diastereoselective synthesis of the ABC rings of (?)‐norzoanthamine has been achieved starting from the (?)‐Hajos–Parrish ketone (see scheme). Three asymmetric quaternary carbon centers on the C ring were constructed by a 1,4‐addition, and an intramolecular Diels–Alder reaction provided a trans‐decalin scaffold on the AB rings.  |
| Keywords: | diastereoselectivity Diels– Alder reaction Michael addition natural products total synthesis |