This review highlights recent innovative synthetic strategies developed for the stereoselective construction of natural complex decalin systems. It offers an insight into various synthetic targets and approaches and provides information for developments within the area of natural products as well as synthetic methodology.
Toward the synthesis of FR225654, an antidiabetic natural product, the Sharpless asymmetric dihydroxylation of chiral bishomoallylic alcohols, never reported in the literature, was examined. Employing the pyrimidine class of ligands, a high level of matched diastereoselectivity was obtained. An application to the stereoselective synthesis of the C1-C10-C5 fragment of FR225654 was performed.
Asymmetric Sharpless Dihydroxylation Reaction of Chiral Bishomoallylic Alcohols: Application to the Synthesis of the C1-C10-C5 Fragment of FR225654. -A series of different ligands is screened for the asymmetric dihydroxylation of bishomoallylic alcohols to produce 1,2,5-pentanetriol derivatives. Product (IIb) is easily transformed into the C1-C10-C5 fragment (IX) of the antidiabetic natural product FR225654. -(MOHAMMAD, S.; DHAMBRI, S.; GORI, D.; VAXELAIRE, C.; SORIN, G.; ARDISSON, J.; LANNOU*, M.-I.; Synlett 24 (2013) 19, 2581-2585, http://dx.doi.org/10.1055/s-0033-1340164 ; CNRS, Fac. Pharm., Univ. Rene Descartes, F-75270 Paris, Fr.; Eng.) -Mais 18-053
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