Synthetic Study of Siccanin, an Antifungal Antibiotic. I. Synthesis of 3, 5a-Dimethyl-1-hydroxy-5, 5a, 6, 7, 8, 8a-hexahydroxanthene

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Refering to the previous work, ²⁾ tetracyclic diol (3a) derived from siccanin (1), an antifungal antibiotic, was converted back into 1; and 3a was shown as an important synthetic intermediate for 1. On the other hand, as a preliminary study on synthesis of 1, cyclization of 1-methyl-2-(2, 6-dihydroxy-4-methylbenzyl)cyclohexanol (19 or 20) or 1-methylene-2-(2, 6-dihydroxy-4-methylbenzyl)cyclohexane (21) was carried out, forming a hexahydroxanthene derivative (23) whose structure involves the B, C, and D rings of siccanin (1).