Synthetic process for the manufacture of ecteinascidin compounds

摘要

This invention relates to compounds of formula II: wherein R1, R2, ProtSH, and ProtNH are as defined, to processes for the synthesis of ecteinascidins of formula I from compounds of formula II, and to processes for the synthesis of compounds of formula II.;

主权项

1. A process comprising the step of reducing a quinone of formula II to form a hydroquinone, followed by alkylation of the resulting hydroquinone with a suitable electrophilic reagent to give a compound of formula IIa: wherein R1 is a protecting group for OH; R2 is selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, C(═O)Ra, C(═O)ORb, C(═O)NRcRd, and a protecting group for amino; Ra is selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic group; Rb is independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, and a protecting group for OH; Rc and Rd are independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, and a protecting group for amino; ProtNH is a protecting group for amino; and ProtsH is a protecting group for SH.