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2005
Other bioactive products
U 1300
Stereoselective Preparation of Trisubstituted (Z)-Alkenes: Synthesis of the
Fragment of (-)-Laulimalide. — The synthesis of fragment (VIII) is
27- 204 C17—C27
based on the unique stereospecific synthesis of (Z)-alkenyl compound (IIIa). The latter
is observed by Kumada—Tamao—Corriu cross-coupling of bromo alkene (I), which
proceeds with inversion of the initial configuration. After transformation of (IIIa) into
the mesylate of alcohol (VII), an intramolecular SN2' reaction accompanied with chirality transfer in the presence of Bu4NF affords the desired fragment of (-)-laulimalide (X)
as inseparable mixture with its epimer (IX). — (UENISHI*, J.; OHMI, M.; MATSUI,
K.; IWANO, M.; Tetrahedron 61 (2005) 8, 1971-1979; Kyoto Pharm. Univ., Misasagi,
Yamashina, Kyoto 607, Japan; Eng.) — Klein
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