David E. Cane Publications 1. E. J. Corey and David E. Cane, "The Synthesis of Olefins from β-Hydroxyphosphonamides. Stereochemistry and Extension to the Formation of Conjugated Dienes," J. Org. Chem., 34, 3053 (1969). 2. E. J. Corey and David E. Cane, "The Metalation-Alkylation of Ynamines," J. Org.Chem., 35, 3405 (1970). 3. E. J. Corey and David E. Cane, "A New Method for the Controlled Hydroxymethylation of Ketones," J. Org. Chem., 36, 3070 (1971). 4. E. J. Corey, David E. Cane, and Lawrence Libit, "The Synthesis of Racemic α-trans- and β-trans-Bergamotene," J. Am. Chem. Soc., 93, 7013, (1971). 5. D. Arigoni, David E. Cane, Beat Mueller and Christopher Tamm, "The Mode of Incorporation of Farnesyl Pyrophosphate into Verrucarol," Helv. Chim. Acta, 56, 2946 (1973). 6. David E. Cane and Ronald H. Levin, "Application of Carbon-13 Magnetic Resonance to Isoprenoid Biosynthesis. I. Ovalicin," J. Am. Chem. Soc., 97, 1982 (1975). 7. David E. Cane and Ronald H. Levin, "Application of Carbon-13 Magnetic Resonance to Isoprenoid Biosynthesis. II. Ovalicin and the Use of Double-Labeled Mevalonate," J. Am. Chem. Soc., 98, 1183 (1976). 8. David E. Cane and Robert B. Nachbar, "Biosynthesis of Fomannosin from [1,2-13C]-Acetate," Tetrahedron Lett. 2097-2100 (1976). 9. David E. Cane and G. G. S. King, "The Biosynthesis of Ovalicin: Isolation of β-trans-Bergamotene," Tetrahedron Lett.., 4737 (1976). 10. David E. Cane and Stephen L. Buchwald, "Application of Deuterium Magnetic Resonance to Biosynthetic Studies I; Biosynthesis of Ovalicin," J. Am. Chem. Soc., 99, 6132 (1977). 11. David E. Cane and Radha Iyengar, "The Absolute Configuration of Cyclonerodiol," Tetrahedron Lett., 3511 (1977). 12. David E. Cane, Robert B. Nachbar, Jon Clardy, and Janet Finer, "The Absolute Configuration of Fomannosin," Tetrahedron Lett., 4277 (1977). 13. David E. Cane and Ming-Shi Shiao, "Biosynthesis of Cyclonerodiol," J. Am. Chem. Soc., 100, 3203 (1978). 14. David E. Cane and Pushpalatha N. Murthy, "Application of Deuterium Magnetic Resonance to Biosynthetic Studies II. Rosenonolactone Biosynthesis and the Stereochemistry of a Biological SN2' Reaction," J. Am. Chem. Soc., 99, 8327 (1977). 15. David E. Cane and Robert B. Nachbar, "Stereochemical Studies of Isoprenoid Biosynthesis. Biosynthesis of Fomannosin from [1,2-13C]-Acetate," J. Am. Chem. Soc., 100, 3208 (1978). 16. David E. Cane and R. Iyengar, "Conversion of Farnesyl and Nerolidyl Pyrophosphate to Cyclonerodiol by a Cell-Free System from Gibberella Fujikuroi," J. Am. Chem. Soc.,100, 3256 (1978). 17. David E. Cane, Radha Iyengar, and Ming-Shi Shiao, "Cyclonerodiol Biosynthesis and the Stereochemistry of the Conversion of Farnesyl to Nerolidyl Pyrophosphate," J. Am. Chem. Soc., 100, 7122 (1978) 18. C. Richard Hutchinson, Amos H. Heckendorf, J. L. Straughn, P. E. Dadonna and David E. Cane, "The Biosynthesis of Camptothecin. III. Definition of Strictosamide as the Penultimate Biosynthetic Precursor Assisted by 13C and 2H NMR Spectroscopy," J. Am. Chem. Soc., 101, 3358 (1979). 19. David E. Cane, Thomas Rossi, and J. Paul Pachlatko, "The Biosynthesis of Pentalenolactone," Tetrahedron Lett., 3639-3642 (1979). 20. David E. Cane and Radha Iyengar, "Carbon-Carbon Bond Cleavage During Lithium Aluminum Hydride Reduction of a Terminal Propargyl Alcohol," Tetrahedron Lett., 2871 (1979). 21. David E. Cane and Thomas Rossi, "The Isolation and Structural Elucidation of Pentalenolactone E," Tetrahedron Lett., 2973 (1979). 22. David E. Cane and Radha Iyengar, "The Enzymatic Conversion of Farnesyl to Nerolidyl Pyrophosphate: Role of the Pyrophosphate Moiety," J. Am. Chem. Soc., 101, 3385-3388[1, 2] (1979). 23. David E. Cane and Robert B. Nachbar, "Biosynthesis of Fomannosin. 2H NMR Evidence Against Postulated Hydride Shifts," Tetrahedron Lett., 21, 432 (l980). 24. David E. Cane, "The Stereochemistry of Allylic Pyrophosphate Metabolism," Tetrahedron Report, Tetrahedron, 36, 1109 (1980). 25. David E. Cane, Radha Iyengar and Ming-Shi Shiao, "Cyclonerodiol Biosynthesis and the Enzymatic Conversion of Farnesyl to Nerolidyl Pyrophosphate," J. Am. Chem. Soc., 103, 914 (1981). 26. David E. Cane, Thomas Rossi, Ann Marie Tillman, and J. Paul Pachlatko, "Stereochemical Studies of 13 2 Isoprenoid Biosynthesis. Biosynthesis of Pentalenolactone from [UL- C6]-Glucose and [6- H2]-Glucose," J. Am. Chem. Soc., 103, 1838 (1981). 27. David E. Cane, "The Biosynthesis of Sesquiterpenes," in "Biosynthesis of Isoprenoid Compounds," Vol 1, J. W. Porter, S. L. Spurgeon, ed., J. W. Wiley & Sons, New York, 1981, pp 283-374 28. David E. Cane, Heinz Hasler, Joan Materna, Nera Cagnoli-Bellavita, Paolo Ceccherelli, Gian Federico Madruzza, and Judith Polonsky, "2H NMR Determination of the Stereochemistry of an Allylic Displacement Reaction in the Biosynthesis of Virescenol B," J. Chem. Soc. Chem. Commun., 280 (1981). 29. David E. Cane, Stephen Swanson, and Pushpalatha P.N. Murthy, "Trichodiene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc., 103, 2136 (1981). 30. C. Richard Hutchinson, Itsuo Kurobane, David E. Cane, Heinz Hasler, and A. G. McInnes, "Biosynthesis of 2 Macrolide Antibiotics IV. Stereochemistry of Hydrogen Labeling of Brefeldin A by [2- H3]-Acetate," J. Am. Chem. Soc., 103, 2477 (1981). 31. David E. Cane, Heinz Hasler, and Tzyy-Chyau Liang, "Macrolide Biosynthesis. Origin of the Oxygen Atoms in the Erythromycins," J. Am. Chem. Soc., 103, 5960 (1981). 32. David E. Cane, Tzyy-Chyau Liang, and Heinz Hasler, "Polyether Biosynthesis. Origin of the Oxygen Atoms of Monensin A," J. Am. Chem. Soc., 103, 5962 (1981). 13 33. Steven J. Gould and David E. Cane, "The Biosynthesis of Streptonigrin from [UL- C6]-D-Glucose. Origin of the Quinoline Quinone," J. Am. Chem. Soc., 104, 343 (1982). 34. David E. Cane, Akio Saito, Rodney Croteau,John Shaskus, and Mark Felton, "The Enzymatic Cyclization of Geranyl Pyrophosphate to Bornyl Pyrophosphate. Role of the Pyrophosphate Moiety," J.Am. Chem. Soc., 104, 5831 (1982). 35. David E. Cane, Tzyy-Chyau Liang, and Heinz Hasler, "Polyether Biosynthesis II. Origin of the Oxygen Atoms of Monensin A," J. Am. Chem. Soc., 104, 7274 (1982). 2 36. Ann Marie Tillman and David E. Cane, "Pentalenolactone F, A New Metabolite Isolated from Streptomyces. Isolation and Structure Elucidation," J. Antibiot., 36, 170-172 (1983). 37. David E. Cane, Walter D. Celmer, and John W. Westley, "A Unified Stereochemical Model of Polyether Structure and Biogenesis," J. Am. Chem. Soc., 105, 3594-3600 (1983). 38. David E. Cane and Ann Marie Tillman, "Pentalenene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate," J. Am. Chem. Soc., 105, 122-124 (1983). 39. David E. Cane, "Enzyme-Level Studies of the Biosynthesis of Natural Products," in "Enzyme Chemistry, Impact and Applications" C. J. Suckling, ed., Chapman and Hall, London, 1984, pp. 196-231. 40. David E. Cane, Heinz Hasler, Paul B. Taylor, and Tzyy-Chyau Liang, "Macrolide Biosynthesis. II. Origin of the Carbon Skeleton and Oxygen Atoms of the Erythromycins," Tetrahedron, 39, 3449 (1983). 41. David E. Cane, Tzyy-Chyau Liang, Louis Kaplan, Mary K. Nallin, Marvin D. Schulman, Otto D. Hensens, Alan W. Douglas, and George Albers-Schonberg, "The Biosynthetic Origin of the Carbon Skeleton and Oxygen Atoms of the Avermectins", J. Am. Chem. Soc., 105, 4110 (1983). 42. David E. Cane, "Cell-Free Studies of Monoterpene and Sesquiterpene Biosynthesis," Biochem. Soc. Trans., 11, 510-516 (1983). 43. R. Croteau, John Shaskus, David E. Cane, Akio Saito, and Conway Chang, "The Enzymatic Cyclization of [1- 18O]Geranyl Pyrophosphate to l-endo-Fenchol," J. Am. Chem. Soc., 106, 1142 (1984). 44. David E. Cane and Chi-Ching Yang, "The Biosynthetic Origin of the Carbon Skeleton and Oxygen Atoms of Nargenicin A1," J. Am. Chem. Soc., 106, 784 (1984). 45. Rodney Croteau and David E. Cane, "Monoterpene and Sesquiterpene Cyclases," in "Methods in Enzymology. Steroids and Isoprenoids," Vol. 110, J. H. Law and H. C. Rilling, eds., Academic Press, New York, 1985; pp 383-405. 46. David E. Cane, Yvonne G. Whittle, and Tzyy-Chyau Liang, "The Biosynthesis of Quadrone and Terrecyclic Acid," Tetrahedron Lett., 25, 1119 (1984). 47. David E. Cane and Pulikkottil J. Thomas, "The Synthesis of (dl)-Pentalenolactones E and F," J. Am. Chem. Soc., 106, 5295 (1984). 48. David E. Cane, Christopher Abell, and Ann Marie Tillman, "Pentalenene Biosynthesis and the Enzymatic Cyclization of Farnesyl Pyrophosphate. Proof that the Cyclization is Catalyzed by a Single Enzyme," Bioorganic Chemistry, 12, 312 (1984). 49. David E. Cane and Chi-Ching Yang, "Nargenicin Biosynthesis. Late Stage Oxidations and Absolute Configuration," J. Antibiot., 38, 423-426 (1985). 50. David E. Cane, Hyun-Joon Ha, Christopher Pargellis, Felix Waldmeier, Stephen Swanson, and Pushpalatha P. N. Murthy, "Trichodiene Biosynthesis and the Stereochemistry of the Enzymatic Cyclization of Farnesyl Pyrophosphate," Bioorganic Chemistry, 13, 246 (1985). 51. David E. Cane, "Isoprenoid Biosynthesis. Stereochemistry of the Cyclization of Allylic Pyrophosphates," Acc. Chem. Res., 18, 220 (1985). 52. Rodney B. Croteau, John J. Shaskus, Britta Renstrom, N. Mark Felton, David E. Cane, Akio Saito, and Conway Chang, "Mechanism of the Pyrophosphate Migration in the Enzymatic Cyclization of Geranyl and Linalyl Pyrophosphate to (+)- and (-)-Bornyl Pyrophosphate," Biochemistry, 24, 7077 (1985). 3 53. David E. Cane, "Stereochemical Studies of Natural Products Biosynthesis," Ann. N. Y. Acad. Sci., 471, 130-137 (1986). 54. David E. Cane,