Flindersia alkaloids, derivatives and analogs: compositions and methods for producing the same
AssigneeUniversity of Houston System
InventorsJeremy A May, Ravikrishna Vallakati
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Abstract
The present invention provides methods for chemically synthesizing naturally-occurring alkaloids, for example, Flindersia alkaloids, and their analogs and derivatives. Generally, the precursor borrerine is synthesized from tryptamine in the presence of an alkylating agent, an acylating agent and a reducing agent and dimerized in the presence of an acid, for example, tetrafluoroacetic acid, hydrochloric acid or acetic acid to yield the products. Analog and derivative compounds are produced by derivatizing one or more of the tryptamine, alkylating agent or acylating agent. Also provided are the synthetic alkaloids and derivatives and analogs thereof produced by the synthetic methods.
Claims21
A method for chemically synthesizing Flinderole A or des-methylflinderole C, comprising the steps of:
- synthesizing borrerine;
- dimerizing said borrerine in the presence of acetic acid or hydrochloric acid, to yield a crude material;
- and
- isolating the Flinderole A or des-methylflinderole C from the crude material.
A chemical synthetic method for producing Flinderole B or Flinderole C, comprising the steps of:
- synthesizing borrerine from tryptamine;
- methylating borrerine with a methylating agent;
- dimerizing the methylated borrerine in the presence of hydrochloric acid or acetic acid to yield a crude material;
- and
- isolating the Flinderole B or Flinderole C from the crude material.
A chemical synthetic method for producing flinderoles, A, B or C comprising the steps of:
- contacting a derivative of 3-methyl-2-butenal with a tryptamine derivative;
- adding an aldehyde derivative of methyl chloroformate in the presence of a base to form an α-substituted piperidinyl-N-carbamate intermediate;
- adding a strong reducing agent to the intermediate to produce a derivative of borrerine;
- wherein, if the flinderole is Flinderole A or des-methylflinderole C, the method further comprises:
- dimerizing the synthesized borrerine derivative in the presence of hydrochloric acid or acetic acid to yield a crude material;
- and
- isolating Flinderole A or des-methylflinderole C from the crude material;
- or
- wherein if the flinderole is Flinderole B or Flinderole C, the method further comprises:
- methylating borrerine with a methylating agent;
- dimerizing the methylated borrerine in the presence of hydrochloric acid or acetic acid to yield a crude material;
- and
- isolating Flinderole B or Flinderole C from the crude material.
Dependencies are inferred from the claim text.