This new program will focus on the development of a novel strategy for the enantioselective synthesis of complex medium ring ether marine natural products. A practical asymmetric aldol addition followed by a ring closing metathesis reaction will be used to construct six to nine membered cyclic ethers. The ring closing metathesis reaction of medium rings can be effected without cyclic constraints by exploiting the gauche effect of adjacent oxygen substituents. This effect will be explored in a tandem ring opening-ring closing metathesis reaction for the simultaneous production of two medium-sized cyclic ethers. The methods for medium ring ether synthesis will be utilized in the synthesis of a variety of novel, pharmacologically active marine natural products such as isolaurallene, pannosallene, brevetoxin A, mucocin and gigantecin. Since many of the polyether toxins and the cytotoxic annonaceous acetogenins are available in very small quantities, chemical synthesis offers one solution to the supply problem for further studies on the mechanism of action and chemical modification of the toxins and antitumor agents, leading ultimately to improvements in public health.
| Crimmins, Michael T; Knight, John D; Williams, Philip S et al. (2014) Stereoselective synthesis of quaternary carbons via the dianionic Ireland-Claisen rearrangement. Org Lett 16:2458-61 |
| Crimmins, Michael T; Hughes, Colin O (2012) Total synthesis of the proposed structure of aldingenin B. Org Lett 14:2168-71 |
| Crimmins, Michael T; Dechert, Anne-Marie R (2012) Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a. Org Lett 14:2366-9 |
| Crimmins, Michael T; Haley, Matthew W; O'Bryan, Elizabeth A (2011) Formal synthesis of (+)-sorangicin A. Org Lett 13:4712-5 |
| Crimmins, Michael T; Stauffer, Christina S; Mans, Mark C (2011) Total syntheses of (+)-vigulariol and (-)-sclerophytin A. Org Lett 13:4890-3 |
| Crimmins, Michael T; Martin, Timothy J; Martinot, Theodore A (2010) Synthesis of the bis-tetrahydropyran core of amphidinol 3. Org Lett 12:3890-3 |
| Crimmins, Michael T; O'Bryan, Elizabeth A (2010) Enantioselective total synthesis of spirofungins A and B. Org Lett 12:4416-9 |
| Crimmins, Michael T; Mans, Mark C; Rodriguez, Abimael D (2010) Total synthesis of the proposed structure of briarellin J. Org Lett 12:5028-31 |
| Crimmins, Michael T; Shamszad, Mariam; Mattson, Anita E (2010) A highly convergent approach toward (-)-brevenal. Org Lett 12:2614-7 |
| Crimmins, Michael T; Ellis, J Michael; Emmitte, Kyle A et al. (2009) Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits. Chemistry 15:9223-34 |
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