Anthracyclinone Ring C Synthesis via Chelate Carbene Complexes

✍ Scribed by Prof. Dr. Karl Heinz Dötz; Dr. Michael Popall

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: English
• Weight: 335 KB
• Volume: 26
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198711581

✦ Synopsis

The generation of I and their reactions with acid chlorides were performed in one flask as typified in the following example (reaction 3 in Table I). A mixture of Zn-Cu couple [I71 ( I 10 mg, 1.7 mmol) and 3-iodopropyl phenyl ketone (356 mg, 1.3 mmol) in dry benzene (4 mL) and HMPA (0.5 mL) was stirred at room temperature for 1 h and then at 40 "C for 1 h under nitrogen. Then, solutions of [Pd(PPh,),] (46 mg, 0.04 mmol) in benzene ( I mL) and octanoyl chloride (163 mg, 1.0 mmol) in benzene (1 mL) were successively added at 40 "C and the mixture was stirred at the same temperature for 2 h. After dilution with ether, successive washing with I N HCI and aqueous NaHC03, and drying over MgSO,, followed by evaporation o f the solvents, the residue was purified by column chromatography over silica gel (hexaneethyl acetate gradient) to provide I-phenyl-1,5-dodecanedione in 80% yield.