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Process for conversion of oxotomaymycin to tomaymycin

  • US 4,427,588 A
  • Filed: 11/08/1982
  • Issued: 01/24/1984
  • Est. Priority Date: 11/08/1982
  • Status: Expired due to Fees
First Claim
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1. A process for the preparation of a compound of the formula ##STR18## which comprises the steps of (1) converting oxotomaymycin of the formula ##STR19## to the corresponding 8-OH protected intermediate of the formula ##STR20## wherein R is a conventional phenolic hydroxyl protecting group;

  • (2) reacting amide intermediate III with phosphorous pentasulfide or 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide in an inert organic solvent to produce the thioamide intermediate of the formula ##STR21## wherein R is as defined above;

    (3) reacting intermediate IV with a (lower)alkyl halide or (lower)alkoxonium salt in an inert organic solvent and in the presence of base to produce the thioiminoether intermediate of the formula ##STR22## wherein R3 is (lower)alkyl and R is as defined above;

    (4) optionally removing the C-8 hydroxyl protecting group of intermediate V to form an intermediate of the formula ##STR23## wherein R3 is as defined above;

    (5) selectively reducing the thioiminoether moiety of intermediate V or intermediate VI in an inert solvent to produce a thiocarbinolamine intermediate of the formula ##STR24## wherein R and R3 are as defined above; and

    (6) reacting intermediate VII or VIII with a mercuric salt in methanol to form the carbinolamine product of the formula ##STR25## wherein R is as defined above; and

    , when the product obtained is compound IX, removing the hydroxyl protecting group R from intermediate IX so as to form the desired tomaymycin product I.

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