Macrolides And Polyethers Extender Groups other than Malonate

The use of propionate as a starter group as in the formation of the anthracyclines is perhaps reduction

CoAS

g x malonyl-CoA

propionyl-CoA

O OH CO2Me

co2h Os

11-hydroxylation

CO2Me reduction of C=O

O OH CO2Me

OH O OH OH E-rhodomycinone

TDP-L-daunosamine

O2 NADPH

CO2Me

O2 NADPH

OH O OH OH aklavinone

TDP-D-glucose

OH O OH OH E-rhodomycinone

TDP-L-daunosamine

OH O OH OH aklavinone

OH O OH O aklanonic acid I SAM I aldol O CO2Me

OH O OH O aklaviketone

OH O OH O aklanonic acid I SAM I aldol O CO2Me

NADPH

OH O OH O aklaviketone r

(i) glycosylation of 7-hydroxyl T (ii) hydrolysis of ester I (iii) decarboxylation of 10-acid I (iv) oxidation to 13-ketone I (v) methylation of 4-hydroxyl

O2 NADPH

hydroxylation OMe O OH O at C-14

daunorubicin (daunomycin)

TDP-D-glucose

O OH

O OH

OMe O OH O

OMe O OH O

I NH2

doxorubicin (adriamycin)

Figure 3.56

4' NH2 [epimer at 4' = epirubicin (4'-epidoxorubicin)]

NADPH

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