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Total synthesis of (-)-norzoanthamine.

Angewandte Chemie (International ed. in English) (2008-12-05)
Daisuke Yamashita, Yoshihisa Murata, Naotsuka Hikage, Ken-Ichi Takao, Atsuo Nakazaki, Susumu Kobayashi
RÉSUMÉ

No bones about it: (-)-Norzoanthamine, a promising candidate for an anti-osteoporotic drug, was the target of a total synthesis (see scheme). The final bisaminal formation with AcOH/H(2)O gave the DEFG ring, while the cyclization precursor was prepared by installing the remaining bisaminal unit after oxidative cleavage of the cyclopentanol moiety.

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Sigma-Aldrich
Cyclopentanol, 99%