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Alkaloid and Terpenoid Diversity in Natural Products
Polycylic structures are found in nearly every biosynthetic class of natural products. In particular, an amazing range of rigid densely functionalized polycylic compounds are formed from simple polyisoprenoid precursors during terpene biosynthesis. Examples include Taxol (a widely used anticancer drug) and the ginkgolides (active ingredients in Ginkgo biloba). Related strategies are used in alkaloid biosynthesis, leading to complex polycyclic products with nitrogen functionalities.
We have developed a diversity-oriented synthesis in which multiple polycyclic scaffolds are synthesized from a small set of relatively simple starting materials. A variety of cyclization reactions are then used to generate diverse polycyclic molecules related to alkaloid and terpenoid natural products.
Publications
Moura-Letts, G.; DiBlasi, C. M.; Bauer, R. A.; Tan, D. S.* “Solid-phase synthesis and chemical space analysis of a 190-membered alkaloid/terpenoid-like library.” Proc. Natl. Acad. Sci. USA 2011, 108, 6745-6750.
[ Abstract | PDF | Supporting Info ]
Bauer, R. A.; DiBlasi, C. M.; Tan, D. S.* “The tert-butylsulfinamide lynchpin in transition-metal-mediated multiscaffold library synthesis.” Org. Lett. 2010, 12, 2084-2087.
[ Abstract | PDF | Supporting Info | PMC ]
DiBlasi, C. M.; Macks, D. E.; Tan, D. S.* “An acid-stable tert-butyldiarylsilyl (TBDAS) linker for solid-phase organic synthesis.” Org. Lett. 2005, 7, 1777-1780.
[ Abstract | PDF | Supporting Info ]
Highlighted in Lett. Org. Chem. (PDF)
News Articles
08/02/2009
Trends in Chemical Biology 2009
NYAS eBriefing
The year-end meeting of the Chemical Biology Discussion Group, held June 1, 2009, highlighted the diverse spokes of chemical biology around a central theme: biomolecular recognition.
[Overview (free) | Meeting report (membership req'd)]
Renato Bauer's seminar: Asymmetric Synthesis of a Multiscaffold Library for Discovery Screening
[Video (membership req'd)]
