Synthesis of 2′-Iodo Analogues of β-Rhodomycins1

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Abstract
10-O-(R/S)Tetrahydropyranosyl-β-rhodomycinone (5a,b) was prepared via 7,9-O-phenylboronyl-β-rhodomycinone (3) from β-rhodomycinone (1). Glycosidation of 5a,b with 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (3,4-di-O-acetyl-L-rhamnal) (6) and 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-L-lyxo-hex-1-enitol (3,4-di-O-acetyl-L-fucal) (7) using N-iodosuccinimide gave the corresponding 7-O-glycosyl-β-rhodomycinones 8a,b, 9a,b and 10a,b, 11a,b. After cleavage of the THP-ether and O-deacetylation 7-O-(2,6-dideoxy-2-iodo-α-L-manno-hexopyranosyl)-β-rhodomycinone (14) and 7-O-(2,6-dideoxy-2-iodo-α-L-talo-hexopyranosyl)-β-rhodomycinone (16) were obtained.