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Organic Synthesis workbook li - Bittner C.

Bittner C. Organic Synthesis workbook li - John Wiley & Sons, 2001. - 292 p.
ISBN: 3-527-30415-0
Download (direct link): bittnerorganicsynthesisworkbook2001.pdf
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6 a) J. D. White, T. S. Kim, M. Nambu, J. Am. Chem. Soc. 1995,
117, 5612-5613; b) D. G. Nagle, R. S. Geralds, H. D. Yoo, W.
H. Gerwick, T. S. Kim, M. Nambu, J. D. White, Tetrahedron Lett. 1995, 36, 1189-1192.
7 a) P. J. Kocienski, Protecting Groups, Georg Thieme Verlag, New York 1994; b) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons, New York 1999.
8 a) J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402-409; Angew. Chem. Int. Ed. Engl. 1976, 15, 333-340; b) L. S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecules, University Science Books, Mill. Valley Calif. 1994; c) R. B. Grossman, The Art of Writing Reasonable Organic Reaction Mechanisms, Springer, New York 1999.
9 P. Wipf, W. Xu, Tetrahedron Lett. 1994, 35, 5197-5200.
10 For a review see: S. D. Burke, R. L. Danheiser (ed.) Handbook of Reagents for Organic Synthesis - Oxidizing and Reducing Agents, John Wiley & Sons, Chichester 1999.
11 E. Negishi, D. R. Swanson, S. R. Miller, Tetrahedron Lett. 1988, 29, 1631-1634.
12 H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 5919-5923.
13 H. C. Brown, U. S. Racherla, Y. Liao, V. V. Khanna, J. Org. Chem. 1992, 57, 6608-6614.
14 a) H. C. Brown, R. S. Randad, K. S. Bhat, M. Zaidlewicz, U. S. Racherla, J. Am. Chem. Soc. 1990, 112, 2389-2392; b) R. Sturmer, R. W. Hoffmann, Synlett 1990, 759-761; c) A. Hafner, R. O. Duthaler, R. Marti, G. Rhis, P. Rothe-Streit, F. Schwarzenbach, J. Am. Chem. Soc. 1992, 114, 2321-2336; d) L. F. Tietze, K. Schiemann, C. Wegner, C. Wulff, Chem. Eur. J. 1996, 2, 1164-1172; e) L. F. Tietze, C. Wulff, C. Wegner, A.
3 Curacin A
53
Schuffenhauer, K. Schiemann, ./. Am. Chem. Soc. 1998, 120, 4276-4280; f) D. R. Gauthier, E. M. Carreira, Angew. Chem. 1996, 108, 2521-2523; Angew. Chem. Int. Ed. Engl. 1996, 35, 2363-2365; g) G. E. Keck, . H. Tarbet, L. S. Geraci, J. Am. Chem. Soc. 1993, 115, 8467-8468; h) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc. 1993, 115, 7001-7002; i) A. Yanagisawa, H. Nakashima, A. Ishiba, H. Yamamoto, J. Am. Chem. Soc. 1996,
118, 4723-4724.
15 H. Finkelstein, Ber. Dtsch. Chem. Ges. 1910, 43, 1528-1532.
16 H. E. Simmons, R. D. Smith, J. Am. Chem. Soc. 1959, 81, 4256-4264.
17 S. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York 1994.
18 a) A. B. Charette, S. Prescott, C. Brochu, J. Org. Chem. 1995, 60, 1081-1083; b) A. B. Charette, H. Juteau, j. Am. Chem. Soc. 1994,116, 2651-2652.
19 a) H. Niwa, S. Ito, T. Hasegawa, K. Wakamatsu, T. Mori, K. Yamada, Tetrahedron Lett. 1991, 32, 1329-1330; b) A. K. Singh, R. S. Varma, Tetrahedron Lett. 1992, 33, 2307-2310.
20 For a review see: A. J. Pearson, W. J. Roush (ed.) Handbook of Reagents for Organic Synthesis - Activating Agents and Protecting Groups, John Wiley & Sons, Chichester 1999.
21 a) B. Neises, W. Steglich, Angew. Chem. 1978, 90, 556-557; Angew. Chem. Int. Ed. Engl. 1978, 77, 522-524; b) A. Hassner, V. Alexanian, Tetrahedron Lett. 1978, 4475-4478.
22 a) G. M. Atkins, Jr., E. M. Burgess, J. Am. Chem. Soc. 1968, 90, 4744-4745; b) P. Wipf, C. P. Miller, Tetrahedron Lett. 1992, 33, 907-910.
23 P. Wipf, C. P. Miller, Tetrahedron Lett. 1992, 33, 6627-6630.
24 P. Wipf, S. Venkatraman, Synlett 1997, 1-10.
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Organic Synthesis Workbook II
C. Bittner, A. S. Busemann, U. Griesbach, F. Haunert, W.-R. Krahnert, A. Modi, J. Olschimke, P. L. Steck
Copyright 2001 Wiley-VCH Verlag GmbH ISBNs: 3-527-30415-0 (Softcover); 3-527-60013-2 (Electronic)
4
Dysidiolide (Corey 1997)
4.1 Introduction
The marine metabolite dysidiolide (1) was isolated from the Caribbean sponge Dysidea etheria de Laubenfels. Dysidiolide is the first naturally derived inhibitor of the human cdc25A protein phosphatase.1,2 Since this class of enzymes (cdc25A, and C) is involved in dephosphorylation of cyclin-dependent kinases, dysidiolide causes growth arrest accompanied by massive apoptosis in several human cancer cell lines.3 The structure was elucidated by Gunasekera, Clardy et al. in 1996.4 Dysidiolide is a ^hydroxy-butenolide of the rearranged sesterterpene class whose [4.4.0] bicyclic nucleus with an array of stereocenters including two quaternary carbons and two axially disposed appendages defines a structurally attractive synthetic target with several total syntheses reported to date.5 This problem is based on the first enantioselective total synthesis of dysidiolide realized by Corey in 1997, which also proved the absolute stereochemistry of natural I.6

1
dysidiolide
56
4 Dysidiolide
4.2 Overview

1. LDA, PhSSPh, HMPA-THF, r.t.,20 min; MCPBA, CH2CI2, -78 C, 2h; (MeO)3P, C6H6, 80 C, 13 h, 69 %
2. TMSLi, HMPA-Et20, -78 C,
3 h, 64 %
3. KH, DMSO, Ph3PCH3Br, r. t., 2 h, 97 %
TMS
/ \ ,Q P
1. PPTS, acetone-H20, 65 C,
2 h, 100%
2. TPSCI, DMAP, 2,6-lutidine, CH2CI2, r.t., 1.5 h, 96%
3. (Ph3P)3RhCl, H2, C6H6, 65 C, 23 h, 76 %
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