By Chiara Ghiron, Russell Thomas
This e-book is made from a sequence of workouts in artificial natural chemistry established round lately released syntheses. every one workout offers a connection with the unique paintings, an artificial scheme during which both buildings or reagents were passed over, a chain of questions about the workout, and regularly references to similar literature and helpful reviews.
The workouts are designed to supply demanding situations for individuals with a variety of backgrounds, from undergraduates to educational employees and commercial staff leaders, they usually allow the readers to extend their vocabulary of artificial variations. Taking a singular technique, this quantity encourages energetic participation; rather than soaking up average recommendations, readers are requested to suggest options to set difficulties. The routines are perfect for workforce discussions of natural chemistry.
Quality: nice experiment, Searchable, now not bookmarked
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A. M Chong and C. Jennings-White, J. Am. Chem. , 1992,114, 974. O' 4 Abstracted with permission from /. Am. Chem. , 1992,114, 974 ©1992 American Chemical Society Discussion Points • Suggest a motive for oxidising compound 2 before the alkylation step d. • Explain the stereoselectivity observed in step h? • What other ester could have directly afforded compound 7 via a Claisen rearrangement? • Suggest a mechanism for the formation of compound 8, obtained upon ozonolysis of vinylsilane 7. 22 16. Stereoselective Total Synthesis of (+)-Artemisinin Further Reading • For an analysis of recent syntheses of artemisinin, see: M.
Gutman and M. Shapira, Adv. Biochem. /Biotechnol, 1995, 52, 87; L. Kvittingen, Tetrahedron, 1994,50, 8253; A. P. G. Kieboom, Biocatalysis, 1990, 357; C. H. Wong, Science, 1989,244, 1145; C. S. Chen and C. J. Sih, Angew. , 1989, 707, 711; A. M. Klibanov, Trends Biochem. , 1989,14, 141. • For a review on the preparation and reactivity of alkenyl-zinc, -copper, and -chromium organometallics, see: P. Knochel and C. J. Rao, Tetrahedron, 1993, 49, 29. • For a review on the Nozaki-Kishi reaction, see: P.
C. Lee, J. Lau, B. F. Lundt, H. Petersen, P. O. S0rensen and H. Th0gersen, Tetrahedron, 1994,50, 8699. sic) Abstracted with permission from Tetrahedron, 1994,50, 8699 ©1994 Elsevier Science Ltd Discussion Points • What governs the selectivity of the bromination of 3-methylthiophene 1? • Propose a mechanism for the rearrangements occuring in step j. • What is the purpose of the catalytic amount of potassium iodide used in step k? Further Reading • For a recent account of the biological profile of tiagabine see: T.
Exercises in Synthetic Organic Chemistry by Chiara Ghiron, Russell Thomas