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US 9,428,524 B2Granted
Synthetic process for the manufacture of ecteinascidin compounds
AssigneePharma Mar, S.A.
InventorsMa Jesús Martin López, Andrés Francesch Solloso, Maria del Carmen Cuevas Marchante
Life of this patent
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Abstract
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.
Claims20
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.
6 more elements
Dependencies are inferred from the claim text.