Small Molecule Libraries

We are participating in the NIH Molecular Libraries Program (MLP) under our grant entitled "Diversity-Oriented Synthesis of Natural Product-based Libraries for the MLSCN" (P41 GM076267). Our novel natural product-based libraries are being submitted to the NIH Molecular Libraries Small Molecule Repository (MLSMR), where they are available to the scientific community for high-throughput screening in the NIH Molecular Libraries Screening Centers Network (MLSCN). Investigators interested in MLSCN screening under the X01 or R03 mechanisms should see program announcements PAR-08-034 or PAR-08-035. The results of these screens are available to the public via the PubChem database.

We are submitting several different natural product-based libraries to the MLSMR. A list of our compounds that are currently available for screening in the MLSCN (updated quarterly) can be accessed via the following LIVE SEARCH LINKS:

All Tan Libraries
Spiroketal (Aliphatic) Library SK1 (48 compounds submitted)
Spiroketal (Benzannulated) Library SK2 (68 compounds submitted)
Polyketide Fragment Library PK1 (74 compounds submitted)

Screening results are now becoming available as well. To access screening data, click on one of the live search links above, then click on the Bioactivity Analysis button on the search results page:

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Full experimental details on the synthesis and purification of these compounds have been published previously in the following papers:

Spiroketal Libraries

These rigid, stereochemically diverse scaffolds from natural products present sidechains along well-defined three-dimensional vectors.

26)	Liu, G.; Wurst, J. M.; Tan, D. S.* "Stereoselective synthesis of benzannulated spiroketals: Influence of the aromatic ring on reactivity and conformation." Org. Lett. 2009, 11, 3670–3673. [ Abstract | PDF | Supporting Info ]

20)	Moilanen, S. B.; Potuzak, J. S.; Tan, D. S.* "Stereocontrolled synthesis of spiroketals via Ti(Oi-Pr)4-mediated kinetic spirocyclization of glycal epoxides with retention of configuration." J. Am. Chem. Soc. 2006, 128, 1792–1793. [ Abstract | PDF | Supporting Info | PMC ]
•	Highlighted in Nature

19)	Potuzak, J. S.; Moilanen, S. B.; Tan, D. S.* "Stereocontrolled synthesis of spiroketals via a remarkable methanol-induced kinetic spirocyclization reaction." J. Am. Chem. Soc. 2005, 127, 13796–13797. [ Abstract | PDF | Supporting Info ]

14)	Moilanen, S. B.; Tan, D. S.* "Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- and diversity-oriented synthesis: New insights into glycal reactivity." Org. Biomol. Chem. 2005, 3, 798–803. [ Abstract | PDF | Supporting Info ]

12)	Potuzak, J. S.; Tan, D. S.* "Synthesis of C1-alkyl and C1-acylglycals from glycals using a B-alkyl Suzuki–Miyaura cross coupling approach." Tetrahedron Lett. 2004, 45, 1797–1801. [ Abstract | PDF | Supporting Info ]

Polyketide Libraries

These structural motifs from natural products exhibit skeletal and conformational diversity.

21)	Shang, S.; Iwadare, H.; Macks, D. E.; Ambrosini, L. M.; Tan, D. S.* "A unified synthetic approach to polyketides having both skeletal and stereochemical diversity." Org. Lett. 2007, 9, 1895–1898. [ Abstract | PDF | Supporting Info | PMC ]

TBDAS Linker for Solid Phase Synthesis

This robust linker is stable to a wide range of organic reaction conditions and is cleaved chemoselectively with fluoride reagents. Click here for more details.

15)	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 Letters in Organic Chemistry [PDF]