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2005
Alkaloids
U 0600
21- 208
Synthetic Studies on (-)-Lemonomycin: Stereocontrolled Construction of the
3,8-Diazabicyclo[3.2.1] Skeleton. — The synthesis of the tetracyclic backbone (XIII)
of (-)-lemonomycin, including the highly strained bicyclo[3.2.1]octane framework is
reported. The approach features the Ugi 4-component reaction using the novel isocyanide (III), which allows the easy preparation of the cyclic enamide (V). The combination of cross-metathesis for the synthesis of allylsilane (VIII) followed by an intramolecular Hosomi—Sakurai type reaction affords the bicyclo[3.2.1]octane framework
(IX) with complete stereoselectivity. — (RIKIMARU, K.; MORI, K.; KAN, T.;
FUKUYAMA*, T.; Chem. Commun. (Cambridge) 2005, 3, 394-396; Grad. Sch.
Pharm. Sci., Univ. Tokyo, Bunkyo, Tokyo 113, Japan; Eng.) — M. Paetzel
2005
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