The main objective of the proposed research is to provide new and innovative synthetic methods that are applicable to the efficient and selective synthases of a wide variety of complex natural products and related organic compounds including those of medicinal and biological interest through exploration and development of organotransition metal chemistry of palladium and some other Group 7 through 11 transition metals. To this end, it is essential to have reciprocally interactive research activities between basic explorations and applications to the synthesis of natural products and related target molecules. Selection of target molecules and execution of their synthesis primarily from the viewpoint mentioned above constitute the second main objective. In some select cases, efforts will be made to synthesize compounds of medicinal interest and provide their samples. This then is the third main objective of the proposed research. Both methodological development and target synthesis will be performed in the following four areas: (1) cyclic carbopalladation, (2) cyclic acylpalladation, (3) cyclic carboxypalladation, and (4) alpha-substitution of enones. The synthesis of various target compounds will be performed. As new and attractive targets become known in the literatures, some such targets will also be selected and synthesized/ This would necessitate omission of some proposed targets and/or deferment of their synthesis as well as deletion, addition and/or modification of research topics to maximize PI's research contributions within the general area of the proposed research.

Agency
National Institute of Health (NIH)
Institute
National Institute of General Medical Sciences (NIGMS)
Type
Research Project (R01)
Project #
2R01GM036792-12A1
Application #
2759799
Study Section
Medicinal Chemistry Study Section (MCHA)
Project Start
1986-07-01
Project End
2002-08-31
Budget Start
1998-12-01
Budget End
1999-11-30
Support Year
12
Fiscal Year
1999
Total Cost
Indirect Cost
Name
Purdue University
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
072051394
City
West Lafayette
State
IN
Country
United States
Zip Code
47907
Wang, Guangwei; Xu, Shiqing; Hu, Qian et al. (2013) Search for highly efficient, stereoselective, and practical synthesis of complex organic compounds of medicinal importance as exemplified by the synthesis of the C21-C37 fragment of amphotericin?B. Chemistry 19:12938-42
Xu, Shiqing; Lee, Ching-Tien; Wang, Guangwei et al. (2013) Widely applicable synthesis of enantiomerically pure tertiary alkyl-containing 1-alkanols by zirconium-catalyzed asymmetric carboalumination of alkenes and palladium- or copper-catalyzed cross-coupling. Chem Asian J 8:1829-35
Xu, Shiqing; Lee, Ching-Tien; Rao, Honghua et al. (2011) Highly(?98%) Stereo- and Regioselective Trisubstituted Alkene Synthesis of Wide Applicability via 1-Halo-1-alkyne Hydroboration-Tandem Negishi-Suzuki Coupling or Organoborate Migratory Insertion Protocol. Adv Synth Catal 353:2981-2987
Wang, Guangwei; Yin, Ning; Negishi, Ei-ichi (2011) Highly stereoselective total synthesis of fully hydroxy-protected mycolactones A and B and their stereoisomerization upon deprotection. Chemistry 17:4118-30
Negishi, Ei-Ichi; Wang, Guangwei; Rao, Honghua et al. (2010) Alkyne elementometalation-Pd-catalyzed cross-coupling. Toward synthesis of all conceivable types of acyclic alkenes in high yields, efficiently, selectively, economically, and safely: ""green"" way. J Org Chem 75:3151-82
Wang, Chao; Xu, Zhaoqing; Tobrman, Tomas et al. (2010) Arylethyne Bromoboration-Negishi Coupling Route to E- or Z-Aryl-Substituted Trisubstituted Alkenes of ?98% IsomericPurity. New Horizon in the Highly Selective Synthesis of Trisubstituted Alkenes. Adv Synth Catal 352:627-631
Negishi, Ei-Ichi; Tobrman, Tomas; Rao, Honghua et al. (2010) Highly(?98%) Selective Trisubstituted Alkene Synthesis of Wide Applicability via Fluoride-Promoted Pd-Catalyzed Cross-Coupling of Alkenylboranes. Isr J Chem 50:696-701
Wang, Guangwei; Negishi, Ei-Ichi (2009) AlCl3-Promoted Facile E-to-Z Isomerization Route to (Z)-2-Methyl-1-buten-1,4-ylidene Synthons for Highly Efficient and Selective (Z)-Isoprenoid Synthesis. European J Org Chem 2009:
Wang, Chao; Tobrman, Tomas; Xu, Zhaoqing et al. (2009) Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling. Org Lett 11:4092-5
Wang, Guangwei; Huang, Zhihong; Negishi, Ei-Ichi (2008) Efficient and selective syntheses of (all-E)- and (6E,10Z)-2'-O-methylmyxalamides D via Pd-catalyzed alkenylation--carbonyl olefination synergy. Org Lett 10:3223-6

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