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- W2327814143 abstract "The enantiospecific synthesis of (-)cinatrin C1 (3) and (+)-cinatrin C3 (5) from the D-arabinose derivative 9 is described. The stereochemistry at C2 was introduced via a chelation-controlled addition of a carbanion to alpha-hydroxy ketone 8. The best selectivity was achieved by use of the Grignard reagent derived from trimethylsilylacetylene. Transformation of the terminal alkyne into methyl ester 17 followed by acetal hydrolysis and selective lactol oxidation gave cinatrin C1 dimethyl ester (7). Base hydrolysis and acid induced relactonization then gave a 1:1 mixture of cinatrins C1 (3) and C3 (5)." @default.
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- W2327814143 date "2003-01-01" @default.
- W2327814143 modified "2023-09-28" @default.
- W2327814143 title "Enantiospecific synthesis of the phospholipase A<sub>2</sub>inhibitors (−)-cinatrin C<sub>1</sub>and (+)-cinatrin C<sub>3</sub>" @default.
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- W2327814143 doi "https://doi.org/10.1039/b308028e" @default.
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