Beyond Natural Products: Synthetic Analogues of Bryostatin 1

Drug Discovery Research: New Frontiers in the Post-Genomic Era

Volumn , Issue , 2006, Pages 125-162

  Wender, Paul A ^a   Baryza, Jeremy L ^a   Hilinski, Michael K ^a   Horan, Joshua C ^a   Kan, Cindy ^a   Verma, Vishal A ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Bryostatin analogue design; Bryostatin analogues with modified spacer domains; C26 des methyl analogue synthesis

Indexed keywords

EID: 84889498840     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470131862.ch6     Document Type: Chapter

References (99)

1. Al-Katib, A. M., Smith, M. R., Kamanda, W. S., Pettit, G. R., Hamdan, M., Mohamed, A. N., Chelladurai, B., and Mohammad, R. M. (1998). Bryostatin 1 down-regulates mdr1 and potentiates vincristine cytotoxicity in diffuse large cell lymphoma xenografts. Clin Cancer Res 4, 1305-1314.
2. Baryza, J. L., Brenner, S. E., Craske, M. L., Meyer, T., and Wender, P. A. (2004). Simplified analogues of bryostatin with anticancer activity display greater potency for translocation of PKCdelta-GFP. Chem Biol 11, 1261-1267.
3. Basu, A., and Lazo, J. S. (1992). Sensitization of human cervical-carcinoma cells to cis-diamminedichloroplatinum( II) by bryostatin-1. Cancer Res 52, 3119-3124.
4. Bear, H. D., Roberts, J., Cornell, D., Tombes, M. B., and Kyle, B. (2001). Adoptive immunotherapy of cancer with pharmacologically activated lymph node lymphocytes: A pilot clinical trial. Cancer Immunol Immunother 50, 269-274.
5. Beck, F.W. J., Eilender, D. S., Dandashi, M. H., Siddiq, F., Snell, D. C., Godmere,M. A., Al-Katib, A. M., and Mohammad, R. M. (2004). Factors affecting bryostatin 1-enhanced 2-CdA cytotoxicity in resistant B-cell chronic lymphocytic leukemia. Int J Mol Med 14, 113-119.
6. Berkow, R. L., and Kraft, A. S. (1985). Bryostatin, a non-phorbol macrocyclic lactone, activates intact human polymorphonuclear leukocytes and binds to the phorbol ester receptor. Biochem Biophys Res Commun 131, 1109-1116.
7. Betz, A., Ashery, U., Rickmann, M., Augustin, I., Neher, E., Sudhof, T. C., Rettig, J., and Brose, N. (1998). Munc13-1 is a presynaptic phorbol ester receptor that enhances neurotransmitter release. Neuron 21, 123-136.
8. Brose, N., Betz, A., and Wegmeyer, H. (2004). Divergent and convergent signaling by the diacylglycerol second messenger pathway in mammals. Curr Opin Neurobiol 14, 328-340.
9. Cahiez, G., Alexakis, A., and Normant, J. F. (1978). Organomagnesium derivatives of terminal alcohols. Tetrahedron Lett 33, 3013-3014.
10. Caloca, M. J.,Wang, H. B., and Kazanietz, M. G. (2003). Characterization of the Rac-GAP (Rac-GTPaseactivating protein) activity of b2-chimaerin, a 'non-protein kinase C' phorbol ester receptor. Biochem J 375, 313-321.
11. Caponigro, F., French, R. C., and Kaye, S. B. (1997). Protein kinase C: Aworthwhile target for anticancer drugs? Anti-Cancer Drugs 8, 26-33.
12. Cartee, L., Maggio, S. C., Smith, R., Sankala, H. M., Dent, P., and Grant, S. (2003). Protein kinase Cdependent activation of the tumor necrosis factor receptor-mediated extrinsic cell death pathway underlies enhanced apoptosis in human myeloid leukemia cells exposed to bryostatin 1 and flavopiridol. Mol Cancer Ther 2, 83-93.
13. Cragg, L. H., Andreeff, M., Feldman, E., Roberts, J., Murgo, A.,Winning, M., Tombes, M. B., Roboz, G., Kramer, L., and Grant, S. (2002). Phase I trial and correlative laboratory studies of bryostatin I (NSC 339555) and high-dose 1-B-D-arabinofuranosylcytosine in patients with refractory acute leukemia. Clin Cancer Res 8, 2123-2133.
14. Curiel, R. E., Garcia, C. S., Farooq, L., Aguero, M. F., and Espinoza-Delgado, I. (2001). Bryostatin-1 and IL-2 synergize to induce IFN-gamma expression in human peripheral blood T cells: Implications for cancer immunotherapy. J Immunol 167, 4828-4837.
15. da Rocha, A. B., Mans, D. R., Regner, A., and Schwartsmann, G. (2002). Targeting protein kinase C: New therapeutic opportunities against high-grade malignant gliomas? Oncologist 7, 17-33.
16. de Vries, D. J., Herald, C. L., Pettit, G. R., and Blumberg, P. M. (1988). Demonstration of sub-nanomolar affinity of bryostatin 1 for the phorbol ester receptor in rat brain. Biochem Pharmacol 37, 4069-4073.
17. Dempsey, E. C., Newton, A. C., Mochly-Rosen, D., Fields, A. P., Reyland,M. E., Insel, P. A., and Messing, R. O. (2000). Protein kinase C isozymes and the regulation of diverse cell responses. Am J Physiol Lung Cell Mol Physiol 279, L429-L438.
18. Do,Y.,Hegde,V. L., Nagarkatti, P. S., and Nagarkatti,M. (2004). Bryostatin-1 enhances the maturation and antigen-presenting ability of murine and human dendritic cells. Cancer Res 64, 6756-6765.
19. Dowlati, A., Lazarus, H. M., Hartman, P., Jacobberger, J. W., Whitacre, C., Gerson, S. L., Ksenich, P., Cooper, B.W., Frisa, P. S., Gottlieb, M., Murgo, A. J., and Remick, S. C. (2003). Phase I and correlative study of combination bryostatin 1 and vincristine in relapsed B-cell malignancies. Clin Cancer Res 9, 5929-5935.
20. Elgie, A. W., Sargent, J. M., Alton, P., Peters, G. J., Noordhuis, P., Williamson, C. J., and Taylor, C. G. (1998). Modulation of resistance to ara-C by bryostatin in fresh blast cells from patients with AML. Leuk Res 22, 373-378.
21. Evans, D. A., Carter, P. H., Carreira, E. M., Charette, A. B., Prunet, J. A., and Lautens, M. (1999). Total synthesis of bryostatin 2. J Am Chem Soc 121, 7540-7552.
22. Farrow, B., Thomas, R. P.,Wang, X. F., and Evers, B. M. (2002). Activation of conventional PKC isoforms increases expression of the pro-apoptotic protein Bad and TRAIL receptors. Int J Gastrointest Cancer 32, 63-72.
23. Gavrielides, M. V., Frijhoff, A. F., Conti, C. J., and Kazanietz, M. G. (2004). Protein kinase C and prostate carcinogenesis: targeting the cell cycle and apoptotic mechanisms. Curr Drug Targets 5, 431-443.
24. Gomez-Fernandez, J. C., Torrecillas, A., and Corbalan-Garcia, S. (2004). Diacylglycerols as activators of protein kinase C. Mol Membr Biol 21, 339-349.
25. Hall, C., Lim, L., and Leung, T. (2005). C1, see them all. Trends Biochem Sci 30, 169-171.
26. Hammond, C., Shi, Y., Mena, J., Tomic, J., Cervi, D., He, L., Millar, A. E., Debenedette, M., Schuh, A. C., Baryza, J. L.,Wender, P. A., Radvanyi, L., and Spaner, D. E. (2005). Effect of serum and antioxidants on the immunogenicity of protein kinase C-activated chronic lymphocytic leukemia cells. J Immunother 28, 28-39.
27. Harada, T., Inoue, A.,Wada, I., Uchimura, J. J., Tanaka, S., and Oku, A. (1993). Stereoselective acetalization of 1,3-alkanediols controlled by intramolecular van-der-Waals attractive interactions and its application to an enantiodifferentiating transformation of sigma-symmetrical 1,3,5-pentanetriols. J Am Chem Soc 115, 7665-7674.
28. Hecker, E. (1978). In T. J. Slaga, A. Sivak, and R. K. Boutwell (Eds.), Carcinogenesis-A Comprehensive Survey, Vol. 2, p. 11.
29. Hennings, H., Blumberg, P. M., Pettit, G. R., Herald, C. L., Shores, R., andYuspa, S. H. (1987). Bryostatin 1, an activator of protein kinase C, inhibits tumor promotion by phorbol esters in SENCAR mouse skin. Carcinogenesis 8, 1343-1346.
30. Hildebrand, M., Waggoner, L. E., Liu, H. B., Sudek, S., Allen, S., Anderson, C., Sherman, D. H., and Haygood, M. (2004). bryA: An unusual modular polyketide synthase gene from the uncultivated bacterial symbiont of the marine bryozoan Bugula neritina. Chem Biol 11, 1543-1552.
31. Joly, G. D., and Jacobsen, E. N. (2002). Catalyst-controlled diastereoselective hetero-Diels-Alder reactions. Org Lett 4, 1795-1798.
32. Kageyama, M., Tamura, T., Nantz, M. H., Roberts, J. C., Somfai, P., Whritenour, D. C., and Masamune, S. (1990). Synthesis of bryostatin-7. J Am Chem Soc 112, 7407-7408.
33. Kamano,Y., Zhang, H. P., Morita, H., Itokawa, H., Shirota, O., Pettit, G. R., Herald, D. L., and Herald, C. L. (1996). Conformational analysis of a marine antineoplastic macrolide, bryostatin 10. Tetrahedron 52, 2369-2376.
34. Kazanietz, M. G. (2002). Novel ''nonkinase'' phorbol ester receptors: The C1 domain connection. Mol Pharmacol 61, 759-767.
35. Keck, G. E., and Krishnamurthy, D. (1998). Catalytic asymmetric allylation reactions: (S)-1-(phenylmethoxy)-4-penten-2-ol. Org Synth 75, 12-18.
36. Kitamura, M., Ohkuma, T., Inoue, S., Sayo, N., Kumobayashi, H., Akutagawa, S., Ohta, T., Takaya, H., and Noyori, R. (1988). Homogeneous asymmetric hydrogenation of functionalized ketones. J Am Chem Soc 110, 629-631.
37. Koehler,M. F. T. (1999). Protein kinase C activators: Structure, function and synthesis. Ph.D. Dissertation, Stanford University.
38. Kraft, A. S., Smith, J. B., and Berkow, R. L. (1986). Bryostatin, an activator of the calcium phospholipiddependent protein kinase, blocks phorbol ester-induced differentiation of human promyelocytic leukemia cells HL-60. Proc Natl Acad Sci USA 83, 1334-1338.
39. Kudinov, Y.,Wiseman, C. L., and Kharazi, A. I. (2003). Phorbol myristate acetate and bryostatin 1 rescue IFN-gamma inducibility of MHC class II molecules in LS1034 colorectal carcinoma cell line. Cancer Cell Int. 3, 4-19.
40. Lahn, M., Kohler, G., Sundell, K., Su, C., Li, S., Paterson, B. M., and Bumol, T. F. (2004). Protein kinase C alpha expression in breast and ovarian cancer. Oncology 67, 1-10.
41. Lippa, B. (1999). The design, synthesis and biological evaluation of the first totally synthetic bryostatin analogues. Ph.D. Dissertation, Stanford University.
42. Lopanik, N., Lindquist, N., and Targett, N. (2004). Potent cytotoxins produced by a microbial symbiont protect host larvae from predation. Oecologia 139, 131-139.
43. Lorenzo, P. S., Beheshti, M., Pettit, G. R., Stone, J. C., and Blumberg, P. M. (2000). The guanine nucleotide exchange factor RasGRP is a high-affinity target for diacylglycerol and phorbol esters. Mol Pharmacol 57, 840-846.
44. Mackay, H. J., and Twelves, C. J. (2003). Protein kinase C: A target for anticancer drugs? Endocr Relat Cancer 10, 389-396.
45. Madani, S., Hichami, A., Legrand, A., Belleville, J., and Khan, N. A. (2001). Implication of acyl chain of diacylglycerols in activation of different isoforms of protein kinase C. FASEB J 15, 2595-2601.
46. Manning, G., Whyte, D. B., Martinez, R., Hunter, T., and Sudarsanam, S. (2002). The protein kinase complement of the human genome. Science 298, 1912-19334.
47. Marsa, L. (2002). The Los Angeles Times February 11, p. S1.
48. Matsui,W., Smith, B. D., Vala, M., Beal, N., Huff, C. A., Diehl, L. F., and Jones, R. J. (2005). Requirement for myeloid growth factors in the differentiation of acute promyelocytic leukaemia. Br J Haematol 128, 853-862.
49. Matthews, S. A., Pettit, G. R., and Rozengurt, E. (1997). Bryostatin 1 induces biphasic activation of protein kinase D in intact cells. J Biol Chem 272, 20245-20250.
50. McGovern, T. M., and Hellberg, M. E. (2003). Cryptic species, cryptic endosymbionts, and geographical variation in chemical defences in the bryozoan Bugula neritina. Mol Ecol 12, 1207-1215.
51. McGown, A. T., Jayson, G., Pettit, G. R., Haran, M. S.,Ward, T. H., and Crowther, D. (1998). Bryostatin 1-tamoxifen combinations show synergistic effects on the inhibition of growth of P388 cells in vitro. Br J Cancer 77, 216-220.
52. Mendola, D. (2003). Aquaculture of three phyla of marine invertebrates to yield bioactive metabolites: Process developments and economics. Biomol Eng 20, 441-458.
53. Mohammad, R. M., Beck, F.W. J., Katato, K., Hamdy, N.,Wall, N., and AlKatib, A. (1998a). Potentiation of 2-chlorodeoxyadenosine activity by bryostatin 1 in the resistant chronic lymphocytic leukemia cell line (WSU-CLL): Association with increased ratios of dCK/5'-NTand Bax/Bcl-2. Biol Chem 379, 1253-1261.
54. Mohammad, R. M., Varterasian, M. L., Almatchy, V. P., Hannoudi, G. N., Pettit, G. R., and AlKatib, A. (1998b). Successful treatment of human chronic lymphocytic leukemia xenografts with combination biological agents auristatin PE and bryostatin 1. Clin Cancer Res 4, 1337-1343.
55. Moune, S., Niel, G., Busquet, M., Eggleston, I., and Jouin, P. (1997). Total synthesis of dolatrienoic acid: A subunit of dolastatin 14. J Org Chem 62, 3332-3339.
56. Mutter, R., and Wills, M. (2000). Chemistry and clinical biology of the bryostatins. Bioorg Med Chem 8, 1841-1860.
57. Noyori, R., Ohkuma, T., Kitamura, M., Takaya, H., Sayo, N., Kumobayashi, H., and Akutagawa, S. (1987). Asymmetric hydrogenation of beta-keto carboxylic esters-A practical, purely chemical access to betahydroxy esters in high enantiomeric purity. J Am Chem Soc 109, 5856-5858.
58. Ohmori, K., Ogawa, Y., Obitsu, T., Ishikawa, Y., Nishiyama, S., and Yamamura, S. (2000). Total synthesis of bryostatin. Angew Chem, Int Ed 39, 2290-2294.
59. Oz, H. S., Hughes, W. T., Rehg, J. E., and Thomas, E. K. (2000). Effect of CD40 ligand and other immunomodulators on Pneumocystis carinii infection in rat model. Microb Pathog 29, 187-190.
60. Parviz, M., Chin, C. S., Graham, L. J., Miller, C., Lee, C., George, K., and Bear, H. D. (2003). Successful adoptive immunotherapy with vaccine-sensitized T cells, despite no effect with vaccination alone in a weakly immunogenic tumor model. Cancer Immunol Immunother 52, 739-750.
61. Pattabiramen, K. (2004). The design, synthesis, and evaluation of guanidine-based molecular transporters. Ph.D. Dissertation, Stanford University.
62. Pettit, G. R., Day, J. F., Hartwell, J. L., and Wood, H. B. (1970). Antineoplastic components of marine animals. Nature 227, 962-963.
63. Pettit, G. R., Herald, C. L., Doubek, D. L., Herald, D. L., Arnold, E., and Clardy, J. (1982). Antineoplastic agents 86. Isolation and structure of bryostatin 1. J Am Chem Soc 104, 6846-6848.
64. Pettit, G. R., Herald, D. L., Gao, F., Sengupta, D., and Herald, C. L. (1991). Antineoplastic agents 200. Absolute-configuration of the bryostatins. J Org Chem 56, 1337-1340.
65. Pettit, G. R., Sengupta, D., Blumberg, P. M., Lewin, N. E., Schmidt, J. M., and Kraft, A. S. (1992). Structural modifications of bryostatin-2. Anti-Cancer Drug Des 7, 101-113.
66. Rabah, D., Grant, S., Ma, C., and Conrad, D. H. (2001). Bryostatin-1 specifically inhibits in vitro IgE synthesis. J Immunol 167, 4910-4918.
67. Ramsdell, J. S., Pettit, G. R., and Tashjian, A. H., Jr. (1986). Three activators of protein kinase C, bryostatins, dioleins, and phorbol esters, show differing specificities of action on GH4 pituitary cells. J Biol Chem 261, 17073-17080.
68. Rhee, J. S., Betz, A., Pyott, S., Reim, K., Varoqueaux, F., Augustin, I., Hesse, D., Sudhof, T. C., Takahashi, M., Rosenmund, C., and Brose, N. (2002). b-phorbol ester-and diacylglycerol-induced augmentation of transmitter release is mediated by Munc13s and not by PKCs. Cell 108, 121-133.
69. Roddie, P. H., Horton, Y., and Turner, M. L. (2002). Primary acute myeloid leukaemia blasts resistant to cytokine-induced differentiation to dendritic-like leukaemia cells can be forced to differentiate by the addition of bryostatin-1. Leukemia 16, 84-93.
70. Rozengurt, E., Rey, O., and Waldron, R. T. (2005). Protein kinase D signaling. J Biol Chem 280, 13205-13208.
71. Sako, T., Yuspa, S. H., Herald, C. L., Pettit, G. R., and Blumberg, P. M. (1987). Partial parallelism and partial blockade by bryostatin-1 of effects of phorbol ester tumor promoters on primary mouse epidermal-cells. Cancer Res 47, 5445-5450.
72. Schaufelberger, D. E., Koleck, M. P., Beutler, J. A., Vatakis, A. M., Alvarado, A. B., Andrews, P., Marzo, L. V., Muschik, G. M., Roach, J., Ross, J. T., Lebherz, W. B., Reeves, M. P., Eberwein, R. M., Rodgers, L. L., Testerman, R. P., Snader, K. M., and Forenza, S. (1991). The large-scale isolation of bryostatin-1 from Bugula neritina following current good manufacturing practices. J Nat Prod 54, 1265-1270.
73. Scheid, C., Prendiville, J., Jayson, G., Crowther, D., Fox, B., Pettit, G. R., and Stern, P. L. (1994). Immunomodulation in patients receiving intravenous Bryostatin 1 in a phase I clinical study: Comparison with effects of Bryostatin 1 on lymphocyte function in vitro. Cancer Immunol Immunother 39, 223-230.
74. Shindo, M., Irie, K., Masuda, A., Ohigashi, H., Shirai,Y., Miyasaka, K., and Saito, N. (2003). Synthesis and phorbol ester binding of the cysteine-rich domains of diacylglycerol kinase (DGK) isozymes. DGKg and DGKb are new targets of tumor-promoting phorbol esters. J Biol Chem 278, 18448-18454.
75. Silinsky, E. M., and Searl, T. J. (2003). Phorbol esters and neurotransmitter release: more than just protein kinase C? Br J Pharmacol 138, 1191-1201.
76. Spitaler, M., Utz, I., Hilbe, W., Hofmann, J., and Grunicke, H. H. (1998). PKC-independent modulation of multidrug resistance in cells with mutant (V185) but not wild-type (G185) P-glycoprotein by bryosratin 1. Biochem Pharmacol 56, 861-869.
77. Stone, J. C., Stang, S. L., Zheng, Y., Dower, N. A., Brenner, S. E., Baryza, J. L., andWender, P. A. (2004). Synthetic bryostatin analogues activate the RasGRP1 signaling pathway. J Med Chem 47, 6638-6644.
78. van Blitterswijk, W. J., and Houssa, B. (2000). Properties and functions of diacylglycerol kinases. Cell Signal 12, 595-605.
79. Wada, R., Suto, Y., Kanai, M., and Shibasaki, M. (2002). Dramatic switching of protein kinase C agonist/antagonist activity by modifying the 12-ester side chain of phorbol esters. J Am Chem Soc 124, 10658-10659.
80. Wall, N. R., Mohammad, R. M., and AlKatib, A. M. (1999). Bax:Bcl-2 ratio modulation by bryostatin 1 and novel antitubulin agents is important for susceptibility to drug induced apoptosis in the human early pre-B acute lymphoblastic leukemia cell line, Reh. Leuk Res 23, 881-888.
81. Wang, Q. M. J., Bhattacharyya, D., Garfield, S., Nacro, K., Marquez, V. E., and Blumberg, P. M. (1999). Differential localization of protein kinaseCdelta by phorbol esters and related compounds using a fusion protein with green fluorescent protein. J Biol Chem 274, 37233-37239.
82. Wang, S. J., Guo, C. Y., Castillo, A., Dent, P., and Grant, S. (1998). Effect of bryostatin 1 on taxol-induced apoptosis and cytotoxicity in human leukemia cells (U937). Biochem Pharmacol 56, 635-644.
83. Wang, S. J.,Wang, Z. L., Dent, P., and Grant, S. (2003). Induction of tumor necrosis factor by bryostatin 1 is involved in synergistic interactions with paclitaxel in human myeloid leukemia cells. Blood 101, 3648-3657.
84. Wang, Z. L., Wang, S. J., Dai, Y., and Grant, S. (2002). Bryostatin 1 increases 1-beta-D-arabinofuranosylcytosine-induced cytochrome c release and apoptosis in human leukemia cells ectopically expressing Bcl-xL. J Pharmacol Exp Ther 301, 568-577.
85. Wender, P. A., and Baryza, J. L. (2005). Identification of a tunable site in bryostatin analogues: C20 bryologs through late stage diversification. Org Lett 7, 1177-1180.
86. Wender, P. A., and Hinkle, K. W. (2000). Synthesis and biological evaluation of a new class of bryostatin analogues: The role of the C20 substituent in protein kinase C binding. Tetrahedron Lett 41, 6725-6729.
87. Wender, P. A., and Lippa, B. (2000). Synthesis and biological evaluation of bryostatin analogues: The role of the A-ring. Tetrahedron Lett 41, 1007-1011.
88. Wender, P. A.,Koehler,K. F., Sharkey, N. A., Dellaquila, M. L., and Blumberg, P. M. (1986). Analysis of the phorbol ester pharmacophore on protein kinase C as a guide to the rational design of new classes of analogues. Proc Natl Acad Sci USA 83, 4214-4218.
89. Wender, P. A., DeBrabander, J., Harran, P. G., Hinkle, K.W., Lippa, B., and Pettit, G. R. (1998a). Synthesis and biological evaluation of fully synthetic bryostatin analogues. Tetrahedron Lett 39, 8625-8628.
90. Wender, P. A., DeBrabander, J., Harran, P. G., Jimenez, J. M., Koehler, M. F. T., Lippa, B., Park, C. M., Siedenbiedel, C., and Pettit, G. R. (1998b). The design, computer modeling, solution structure, and biological evaluation of synthetic analogues of bryostatin 1. Proc Natl Acad Sci USA 95, 6624-6629.
91. Wender, P. A., Hinkle, K. W., Koehler, M. F. T., and Lippa, B. (1999). The rational design of potential chemotherapeutic agents: Synthesis of bryostatin analogues. Med Res Rev 19, 388-407.
92. Wender, P. A., Baryza, J. L., Bennett, C. E., Bi, C., Brenner, S. E., Clarke, M. O., Horan, J. C., Kan, C., Lacote, E., Lippa, B., Nell, P. G., and Turner, T.M. (2002). The practical synthesis of a novel and highly potent analogue of bryostatin. J Am Chem Soc 124, 13648-13649.
93. Wender, P. A.,Koehler,M. F., and Sendzik, M. (2003a). Anewsynthetic approach to the C ring of known as well as novel bryostatin analogues. Org Lett 5, 4549-4552.
94. Wender, P. A., Mayweg, A. V. W., and Van Deusen, C. L. (2003b). A concise, selective synthesis of the polyketide spacer domain of a potent bryostatin analogue. Org Lett 5, 277-279.
95. Wender, P. A., Baryza, J. L., Brenner, S. E., Clarke, M. O., Craske, M. L., Horan, J. C., and Meyer, T. (2004). Function oriented synthesis: The design, synthesis, PKC binding and translocation activity of a new bryostatin analog. Curr Drug Discov Tech 1, 1-11.
96. Wender, P. A., Clarke, M. O., and Horan, J. C. (2005a). Role of the A-ring of bryostatin analogues in PKC binding: Synthesis and initial biological evaluation of new A-ring-modified bryologs. Org Lett 7, 1995-1998.
97. Wender, P. A., Hilinski, M. K., and Mayweg, A. V. (2005b). Late-stage intermolecular CH activation for lead diversification: A highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues. Org Lett 7, 79-82.
98. Yu, C. M., Choi, H. S., Yoon, S. K., and Jung,W. H. (1997). Effects of subjoin Lewis acid on the catalytic asymmetric allylic transfer reactions of aldehydes promoted by BINOL-Ti(IV) complex. Synlett, 889-890.
99. Zhao, M. Z., Li, J., Mano, E., Song, Z. G., Tschaen, D. M., Grabowski, E. J. J., and Reider, P. J. (1999). Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed byTEMPOand bleach. J Org Chem 64, 2564-2566.