Title

Studies Toward the Total Synthesis of Clavatadine A

Document Type

Oral Presentation

Location

SURC 202

Start Date

17-5-2012

End Date

17-5-2012

Abstract

Clavatadine A, recently isolated from the marine sponge Suberea clavata, is a specific and potent inhibitor of factor XIa. Factor XIa is a component of the coagulation cascade required for the formation of blood clots and is a potential target for treatment of cardiovascular disease. Our efforts to complete the first total synthesis of clavatadine A feature the carbamoylation of a phenol, prepared by dibromination of homogentisic acid lactone, and an azidoisocyanate, derived from ethyl 5-bromovalerate. From our advanced carbamate intermediate, we envision completing the synthesis of clavatadine A by guanylation and lactone hydrolysis.

Faculty Mentor(s)

Stephen Chamberland

Additional Mentoring Department

Chemistry

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Studies Toward the Total Synthesis of Clavatadine A

SURC 202

Clavatadine A, recently isolated from the marine sponge Suberea clavata, is a specific and potent inhibitor of factor XIa. Factor XIa is a component of the coagulation cascade required for the formation of blood clots and is a potential target for treatment of cardiovascular disease. Our efforts to complete the first total synthesis of clavatadine A feature the carbamoylation of a phenol, prepared by dibromination of homogentisic acid lactone, and an azidoisocyanate, derived from ethyl 5-bromovalerate. From our advanced carbamate intermediate, we envision completing the synthesis of clavatadine A by guanylation and lactone hydrolysis.