スルガトキシン合成に関するモデル実験(第7報)スルガトキシンに対応するエチルエステル誘導体とその立体異性体の合成その2

概要

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Four stereoisomeric ethyl esters 6a-d of the debromo-aglycone of surugatoxin (1) were synthesized. Individual treatment of the cis-diols 4β and 4α with borane-pyridine complex in AcOH followed by hydrogenolysis (H_2/Pd-C) of the resulting monools 5c and 5d gave isomeric surugatoxin analogues 6c and 6d, respectively. Heating 5d (or 5c) in 90% trifluoroacetic acid at 60℃ for 6 h resulted in the formation of an equilibrium mixture of desired natural surugatoxin analogue 6a (30%) and its C_4-epimer 6b (3%) together with a 3,4-dehydrated derivative 7 (50%). However, the equilibrium was unfavorable for the natural isomer 6a, the yield of which was raised up to 65% by recycling the recovered dehydrated derivative 7 and 6b.
社団法人日本薬学会の論文
1985-04-25