ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 36, Number 6
JKCSEZ 36(6)
December 20, 1992 

Total synthesis of 9,10-dideoxyrhodomycinone(30) which is the late-stage precursor of naturally occuring β-rhodomycinone(1) is described. After phthalide sulfone 4 was converted to naphthalide sulfone 12 by the several step. Michale addition of naphthalide sulfone 12 which was converted to an anion with 5-ethyl-1,3-cyclohexenone(21) gave a good yield of linearly condensed tetracyclic ketone compound 26. The keto group of 26 was reduced with sodium borohydride and protected by methyl group to afford compound 28. 9,10-Dideoxy-β-rhodomycinone(30) was synthesized from pentamethoxy tetracyclic compound 28 by oxidative demethylation and demethylation of 29.