- Asymmetric synthesis of ES-285, an anticancer agent isolated from marine sources
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The asymmetric synthesis of (2S,3R)-2-amino-3-octane-decanol hydrochloride (ES-285-HC1) was achieved in eight steps in ca. 38% overall yield from the N-benzylimine-derived from. (R)-2,3-O-isopropylidene glyceraldehyde, which is easily available on gram sc
- Allepuz, Ana C.,Badorrey, Ramon,Diaz-de-Viliegas, Maria D.,Galvez, Jose A.
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experimental part
p. 6172 - 6178
(2010/03/26)
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- Ready access to stereodefined β-hydroxy-γ-amino acids. Enantioselective synthesis of fully protected cyclohexylstatine
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A convenient entry to enantiopure syn or anti β-hydroxy-γ-amino acids is described. The starting compounds for the synthesis, anti 3-amino-1,2-diols, are readily available in high enantiomeric purity through catalytic asymmetric epoxidation of an allylic alcohol and titanium-promoted oxirane opening. After adequate protection of the nitrogen, a stereodivergent sequence leads to both anti and syn N-Boc aminoalkyl epoxides. Subsequent regioselective ring-opening with cyanide, protection of the resulting secondary alcohol and nitrile to carboxyl conversion afford, in good yields, protected β-hydroxy-γ-amino acid belonging to either the anti (erythro) or syn (threo) series. This methodology has been applied to the enantioselective preparation of cyclohexylstatine, a key component of several aspartyl protease inhibitors, in fully protected form.
- Castejon, Patricia,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni
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p. 7063 - 7086
(2007/10/03)
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