Publications (9)68.23 Total impact
- ChemInform 03/2010; 33(9):no-no.
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ABSTRACT: The key building blocks (6, 7, and 8) for the intended construction of the originally proposed structures of azaspiracid-1, a potent marine-derived neurotoxin, were coupled and the products elaborated to the targeted compounds (1a,b) and their C-20 epimers (2 and 3). The assembly of the three intermediates was accomplished by a dithiane-based coupling reaction that united the C(1)-C(20) (7) and C(21)-C(27) (8) fragments, followed by a Stille-type coupling which allowed the incorporation of the C(28)-C(40) fragment (6) into the growing substrate. Neither of the final products (1a,b) matched the natural substance by TLC or (1)H NMR spectroscopic analysis, suggesting one or more errors in the originally proposed structure for this notorious biotoxin.Journal of the American Chemical Society 03/2006; 128(7):2258-67. · 11.44 Impact Factor
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ABSTRACT: Syntheses of the three key building blocks (65, 98, and 100) required for the total synthesis of the proposed structure of azaspiracid-1 (1a) are described. Key steps include a TMSOTf-induced ring-closing cascade to form the ABC rings of tetracycle 65, a neodymium-catalyzed internal aminal formation for the construction of intermediate 98, and a Nozaki-Hiyama-Kishi coupling to assemble the required carbon chain of fragment 100. The synthesized fragments, obtained stereoselectively in both their enantiomeric forms, were expected to allow for the construction of all four stereoisomers proposed as possible structures of azaspiracid-1 (1a-d), thus allowing the determination of both the relative and absolute stereochemistry of the natural product.Journal of the American Chemical Society 03/2006; 128(7):2244-57. · 11.44 Impact Factor
- Angewandte Chemie International Edition 09/2003; 42(31):3643-8. · 11.34 Impact Factor
- Angewandte Chemie 07/2003; 115(31):3771 - 3776.
Article: Synthesis of the ABCD Ring System of Azaspiracid We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. This work was financially supported by the National Institutes of Health (USA), The Skaggs Institute for Chemical Biology, a predoctoral fellowship from Bristol-Myers Squibb (to F.B.), postdoctoral fellowships from The Skaggs Institute for Research (to W.Q.), the Academy of Finland, the Ella and Georg Ehrnrooth Foundation and the Tauno TAngewandte Chemie International Edition 12/2001; 40(21):4068-4071. · 11.34 Impact Factor
- Angewandte Chemie International Edition 10/2001; 40(21):4068 - 4071. · 11.34 Impact Factor
Article: Synthesis of the FGHI Ring System of Azaspiracid We thank Dr. D. H. Huang and Dr. G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. Financial support for this work was provided by The Skaggs Institute for Chemical Biology, the National Institutes of Health (USA), a predoctoral fellowship from Bristol-Myers Squibb (F.B.), postdoctoral fellowships from the Academy of Finland, the Ella and Georg Ehrnrooth Foundation, and the Tauno Tönning Foundation (all to P.M.P.),Angewandte Chemie International Edition 06/2001; 40(9):1573. · 11.34 Impact Factor
- Angewandte Chemie 03/2001; 113(7):1302 - 1305.
The Scripps Research Institute
La Jolla, California, United States
- Skaggs Institute for Chemical Biology