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cyclobutadiene cycloadditions with imines
[2+2+1] Cycloadditions
Cacospongionolide B
5-8-5 Ring Systems
5-7 Ring Systems
Tandem Methathesis Olefin Isomerization
Catalytic Asymmetric Synthesis of Amines



Researchers - Atwood Cheung, Ryan Murelli

Atwood CheungCacospongionolide B, a marine sponge metabolite, exhibits potent cytotoxic and antimicrobial activities, and is of keen interest due to its potent immunosuppresive and anti-inflammatory properties. We have completed the first enantioselective total synthesis of cacospongonolide B.  Key to the preparation of the natural product is a three-step sequence initiated by the reductive alkylation of vinyl ketone and bicyclic enone precursors.  Bis-olefination of the resulting diketone provides the triene substrate for a selective ring-closing metathesis reaction that yields the cacospongionolide carbon skeleton. Comparison of theRyan Murelli proton NMR spectrum with an authentic sample confirmed the first synthetic preparation of the natural product.  Efforts to prepare analogs to investigate the processes of inflammation are underway.

Cacospongionolide B

Merkert Chemistry Center, Rms 337 & 339
Tel 617.552.1778, and 617.552.3609
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