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TETRAHEDRON LETTERS
卷 43, 期 37, 页码 6609-6611出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)01459-4
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An enantioselective formal synthesis of the proteasome inhibitor (+)-lactacystim has been achieved using an alkylidene carbene 1,5-CH insertion reaction as a key step. The key cyclisation precursor was synthesised in high diastereomeric excess using a combination of known procedures, with the two key asymmetric centres being introduced via a Sharpless asymmetric epoxidation reaction. KHMDS induced 1,5-CH insertion produced a 3-pyrroline product, which was oxidised to the corresponding 3-pyrrolin-2-one using (1) TPAP/NMO; (2) NaCIO2; (3) NaBH4. The formal synthesis was then completed with a few standard functional group interconversions. (C) 2002 Published by Elsevier Science Ltd.
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