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ChemInform Abstract: Asymmetric Synthesis of the C(18)-C(24) Unit of Lasonolide A.

✍ Scribed by M. NOWAKOWSKI; H. M. R. HOFFMANN

Publisher
John Wiley and Sons
Year
2010
Weight
30 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

Asymmetric Synthesis of the C(18)-C(24) Unit of Lasonolide A. -The synthesis of the title compound (VIII) proceeds with high chiral efficiency. In six steps, four chiral centers are assembled. A key step is the modified Simpkins-Koga asym. deprotonation of compound (I). The strategy outlined is versatile and has potential for constructing other C-glycosides and sugar mimics occurring in marine natural products. -(NOWAKOWSKI, M.; HOFFMANN,

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The C1-C16-segment of lasonolide A has been prepared stereoselectively in high chemical and optical yield starting from 2Ξ±-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (rac-1).