Illudin analogs, uses thereof, and methods for synthesizing the same
AssigneeLantern Pharma Inc.
InventorsGregory J. Tobin, Shawn T. Blumberg, Andrey D. Malakhov
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Abstract
This invention provides illudin derivatives, intermediates, preparation methods, pharmaceutical compositions and uses thereof. Specific examples include novel synthetic routes to prepare illudin derivatives and an illudin derivative having a positive optical rotation, which has therapeutic value.
Claims15
A process for synthesizing compounds having the formula (III):
- wherein Ri, R2 and R3 are independently (C1-C4) alkyl, methyl, or hydroxyl, comprising the steps of
- selecting a cyclopentenone having an alcohol group;
- protecting the alcohol group;
- reacting the protected cyclopentenone with a diazoketone to form a cycloadduct;
- and reducing the cycloadduct.
A method for synthesizing enantiopure acylfulvene, hydroxymethyl acylfulvene (HMAF), and hydroxyureamethylacylfulvene (UMAF) utilizing an enzymatic resolution of Compound 9 (Scheme 5).
A method of synthesizing hydroxyureamethylacylfulvene (+) comprising the steps of:
- a) selecting a cyclopentenone having an alcohol group;
- b) protecting the alcohol group of the selected cyclopentenone;
- c) reacting the protected cyclopentenone with a diazoketone to form a cycloadduct;
- d) Reducing the cycloadduct obtained in step c;
- e) Alkylating a ketone group of the reduced cycloadduct;
- f) Cleaving an oxy group of the alkylated cycloadduct;
- and
- g) Oxidizing the cleaved cycloadduct to obtain hydroxyureamethylacylfulvene (+).
Dependencies are inferred from the claim text.