The long-term objective of this research program is to advance the practice of complex molecule synthesis. Special emphasis is placed on natural products that contain nitrogen since an unusually large number of pharmacologically active compounds incorporate this element within their structure. Despite the many advances in organic synthesis in the past 20th century the efficient and economical synthesis of complex natural products remains a challenging endeavor. Our plan is to introduce new inexpensive building blocks to the field of organic synthesis for use in asymmetric synthesis of nitrogen heterocycles. These building blocks would expedite the chemical synthesis of the rare marine alkaloid upenamide, the stemona alkaloids and 2-substituted piperidine alkaloids. We also present a plan for the synthesis of Iomaiviticins A and B, secondary metabolites isolated from fermentation of a marine derived actinomycetes. Lomaiviticins A and B are potent antibiotics against Gram-positive bacteria Staphylococcus aureus and Enterococcus faecium (MIC 6-25 ng/spot). An unusual structural feature of the Iomaiviticins is the incorporation of two diazo groups within their structure.
| Smith, Brian J; Sulikowski, Gary A (2010) Total synthesis of (+/-)-haliclonacyclamine C. Angew Chem Int Ed Engl 49:1599-602 |
| Zhang, Weidong; Baranczak, Aleksandra; Sulikowski, Gary A (2008) Stereocontrolled assembly of the C3/C3'dideoxy core of lomaiviticin A/B and congeners. Org Lett 10:1939-41 |
| Luo, Zhushou; Peplowski, Katherine; Sulikowski, Gary A (2007) Formation of the BC ring system of upenamide via a Staudinger/aza-Wittig reaction. Org Lett 9:5051-4 |
| Doroh, Brandon; Sulikowski, Gary A (2006) Progress toward the total synthesis of Bielschowskysin: a stereoselective [2+2] photocycloaddition. Org Lett 8:903-6 |
| Kiewel, Kurt; Luo, Zhushou; Sulikowski, Gary A (2005) Stereocontrolled synthesis of the DE ring system of the marine alkaloid upenamide. Org Lett 7:5163-5 |
