Stereocontrolled Chlorination in Natural Product Synthesis
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1 Stereocontrolled Chlorination in Natural Product Synthesis H H )-napyradiomycin A1 Christian Nilewski, Roger W. Geisser and Erick M. Carreira Nature, 2009, 457, Scott A. Snyder, Zhen-Yu Tang, and Ritu Gupta J. Am. Chem. Soc. 2009, 131, Current Literature Chenbo Wipf Group Aug Chenbo Wipf Group Page 1 of 15 10/3/2009
2 Naturally ccurring rganochlorine Compounds Chlorosulpholipid Cytotoxins Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1999, 121, Ciminiello, P.; Fattorusso, E. Eur. J. rg. Chem. 2004, For a review, see: Gribble, G. R. Acc. Chem. Res. 1998, 31, Chenbo Wipf Group Page 2 of 15 10/3/2009
3 Alcohols to Chlorides: Total Synthesis of (+)-btusenyne H TES TBS P(ct) 3,CBr 4,PhCH 3,86%. Br TES TBS 1. TBAF; 91% 2. P(ct) 3, C 4, 1-methylcyclohexene, PhCH 3 ;70%. 6:1 :elimination Br (+)-obtusenyne NMe 2 - H TBDPS Ghosez reagent py,; 100% TBDPS NMe 2 - RH + - R NMe 2 NMe 2 + R Crimmins, M. T. and Powell, M. T. J. Am. Chem. Soc. 2003, 125, Holmes, A. B. et al Chem. Eur. J. 2008, 14, Holmes, A. B. et al Chem. Commun., 1997, Chenbo Wipf Group Page 3 of 15 10/3/2009
4 Epoxides to Chlorides: Total Synthesis of (+)-Intricatetraol Morimoto, Y; kita, T; Takaishi, M. and Tanaka, T, Angew. Chem. Int. Ed. 2007, 46, Chenbo Wipf Group Page 4 of 15 10/3/2009
5 Epoxides to Chlorides: Towards the Total Synthesis of Chlorosulpholipid Cytotoxins Yoshimitsu, T.; Fukumoto, N. and Tanaka, T. J. rg. Chem. 2009, 74, Chenbo Wipf Group Page 5 of 15 10/3/2009
6 lefin to Vicinal Dichlorides: Total Synthesis of a Plocamium Natural Product Whitney, J. M.; Parnes, J. S. and Shea, K. J. J. rg. Chem. 1997, 62, Chenbo Wipf Group Page 6 of 15 10/3/2009
7 Chlorosulpholipid Cytotoxins Disulphate 1 and vinyl sulphate 2 have been isolated from chromonas danica and Poteriochromonas malhamensis, respectively, and their configurations have not been assigned. Lipids 3 5 have been extracted from digestive glands of contaminated shellfish Mytilus galloprovincialis along the Adriatic coast of Italy and are associated with seafood poisoning. They have been configurationally assigned by NMR spectroscopy using J-based configuration analysis. Elovson, J. & Vagelos, P. R. Biochemistry , Chen, J. L., Proteau, P. J., Roberts, M. A. & Gerwick, W. H. J. Nat. Prod. 1994, 57, Ciminiello, P. et al. J. rg. Chem , Ciminiello, P. et al. J. Am. Chem. Soc. 2002, 124, Ciminiello, P. et al. Tetrahedron 2004, 60, Chenbo Wipf Group Page 7 of 15 10/3/2009
8 lefin to Vicinal Dichlorides: Towards the Total Synthesis of Chlorosulpholipid Cytotoxins Shibuya, G. M.; Kanady, J. S. and Vanderwal, C. D. J. Am. Chem. Soc. 2008, 130, Chenbo Wipf Group Page 8 of 15 10/3/2009
9 Title Paper: Total Synthesis of a Chlorosulpholipid Cytotoxin- 1 st Genneration Approach Chenbo Wipf Group Page 9 of 15 10/3/2009
10 Title Paper: Total Synthesis of a Chlorosulpholipid Cytotoxin- 2 nd Genneration Approach Chenbo Wipf Group Page 10 of 15 10/3/2009
11 Enatioselective Chlorination of Aldehydes M. P. Brochu, S. P. Brown and D. W. C. MacMillan, J. Am. Chem. Soc., 2004, 126, 4108; M. Marigo, A. Braunton, S. Bachmann, M. Marigo and K. A. Jørgensen, J. Am. Chem. Soc., 2004, 126, 4790 Chenbo Wipf Group Page 11 of 15 10/3/2009
12 Napyradiomycins Isolated from terrestrial strains of Streptomyces bacteria Characterized by spectroscopic,degradative, and X-ray crystallographic means. Biological profiles include activity as nonsteroidal estrogen antagonists, antibacterial activity against methicillin- and vancomycin-resistant strains and antitumor potency against colon carcinoma cells Shiomi, K.; Nakamura, H.; Iinuma, H.; Naganawa, H.; Takeuchi, T.; Umezawa, H.; Iitaka, Y. J. Antibiot. 1987, 40, (b) Shiomi, K.; Iinuma, H.; Naganawa, H.; Isshiki, K.; Takeuchi, T.; Umezawa, H.; Iitaka, Y. J.Antibiot. 1986, 39, 494 Chenbo Wipf Group Page 12 of 15 10/3/2009
13 Racemic Total Synthesis of Napyradiomycin A1 Tatsuta, K.; Tanaka, Y.; Kojima, M.; Ikegami, H. Chem. Lett. 2002, 14 Chenbo Wipf Group Page 13 of 15 10/3/2009
14 Title Paper: Enatioselective Chlorination in the Total Synthesis of Napyradiomycin A1 Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986,108, Chenbo Wipf Group Page 14 of 15 10/3/2009
15 Title Paper: Completion of Synthesis H 1. KAc, 18-crown-6; 85% 2. NaH, Me 2 S 4 ;79% 3. Sm, I 2, MeH; 95% Me H CH 3 C(Me) 3,PhMe, propionic acid; 130 o C, 15 h; 27% + 68% SM Me MM MM MM C 2 Me PPh 3 I - 1. KBHPh 3 ;54% 2. DIBAL; 3. DMP; 63% MM Me H 1. BuLi; 34% + 50%SM 2. KHMDS, NCS; 84% MM Me 1. MgI 2,Et 2 /THF 2. PPTS; 90% H 1.7:1 E/Z H )-napyradiomycin A1 Chenbo Wipf Group Page 15 of 15 10/3/2009
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