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Communication | Regular issue | Vol 36, No. 12, 1993, pp.2681-2686
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6539
Synthesis of 3-(1’-Indanylidene)phthalides via Wittig-Horner Reaction of Dimethyl Phthalide-3-phosphonates and Their Conversion to the BCDE Ring Part of Fredericamycin A

Mitsuaki Watanabe,* Hitoshi Morimoto, and Sunao Furukawa

*Center for Instrumental Analysis, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


Wittig-Horner reaction of dimethyl phthalide-3-phosphonates with 1-indanones in the presence of bases was investigated. The 3-(1’-indanylidene)phthalides obtained above were transformed into dibenzo-1,4-diketospiro[4.4]nonanes, the BCDE ring system of fredericamycin A, by consecutive treatments with diisobutylaluminum hydride and pyridinium dichromate.