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For total synthesis of stagonolides and related molecules from other groups see
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4). Evaporation of the solvent yielded the crude cyanohydrin which was purified by chromatography. Preparation of HCN in DIPE: NaCN (10 g) and citric acid (0.1 g) were dissolved in water (100 mL). The solution was cooled in an ice/water bath and extracted with DIPE (50 mL), while acidifying with 33% HCl until pH 5.5. The water layer, which contained a suspension of NaCl, was extracted twice with DIPE (25 mL). The combined DIPE layers were stored in a dark bottle. The above procedure must be performed in a well ventilated fume hood with proper glass ware and hand wares (gloves).
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4 and filtered through celite. The crude mixture was purified by flash chromatography (pet ether/ethyl acetate: 5:1) afforded the compound 11 with 76% yield. Formation of a minor diastereomer was indicated in TLC and was separated by chromatography (de = 19:1).
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