Enantioselective Synthesis of (+)-Cephalostatin 1
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1 1 Cephalostatin 1 Enantioselective Synthesis of (+)-Cephalostatin 1 Tingting Mo Wipf Group Current Lit. Dec Tingting Wipf Group Page 1 of 9 /28/2009
2 2 Background 1972, marine worm Cephalodiscus gilchristi was collected in Indian cean off Southeast Africa 1974, methanol and water extracts of C. gilchristi showed activity towards P388 leukemia ED 50 = ng/ml 1988, the active constituent, Cephalostatin 1 was isolated and its structure was elucidated. The average GI 50 (Growth Inhibition of 50%) against the CI-60 is 1.8 nm. Sufficient amounts of Cephalostatin through synthesis elucidate its cellular target determine its efficacy in vivo for the treatment of cancer. Pettit. G. R.; Inoue, M.; Kamano, Y.; erald, D. L.; Arm, C.; Dufresne, C.; Christie,. D.; Schmidt, J. M.; Doubek, D. L.; Krupa, T. S. J. Am. Chem. Soc. 1988, 110, CI-60 data are available at Tingting Wipf Group Page 2 of 9 /28/2009
3 3 Previous Total Synthesis Western half Unsymmetrical pyrazine coupling From hecogenin acetate 6 Cephalostatin 1 Eastern half From hecogenin acetate 6 Ac 6 azidoketone Western half Me aminomethoxime Eastern half Bu 2 SnCl 2 Benzene PVP o C 3 Me Me Me Me Me 1 LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 0, 692. Jeong, J. U.; Sutton, S. C. Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, Tingting Wipf Group Page 3 of 9 /28/2009
4 5 Title paper: Synthesis of Western alf 5 thermodynamically favored 23 spiroketal E C D A 3 B Western half 5 F spiroketal reorganization Me group oxidation h! 16 deoxygenation 3 Ac olefin installation hecogenin acetate 6 Me group selective allylic oxidation 18 Ac lumihecogenin acetate 7 [] Prins 5 Ac 8 Ac 9 h! 6 1,4-dioxane 7 Selective allylic oxidation 8 Compound 7 is tetrasubstituted Four other allylic hydrogens: two mehines and one methylene Se 2 led to hydroxylation of the methylene Radical halogenations were poorly regioselective Transition metal-catalyzed allylic oxidation gave no reaction Bhandaru, S.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, Bladon, P.; McMeekin, W.; Williams, I. A. J. Am. Chem. Soc. 1963, 85, Tingting Wipf Group Page 4 of 9 /28/2009
5 6 h! 6 1,4-dioxane Ac Ac Title paper: Synthesis of Western alf aac DMF, 100 o C 69% PTAD DCE 61% 2 steps C [2,3]-sigmatropic rearrangerment aza-ene reaction Ac C 1) C(Me) 3, Ts, Me 2) I(Ac) 2 MeC/ 2, 0 o C 57% 2 steps Ac I (Me) 2 C (Me) 2 C Ac (Me) 2 C C 14 Tingting Wipf Group Page 5 of 9 /28/2009
6 7 Title paper: Synthesis of Western alf 5 Ac (Me) 2 C 1) PCC 2) DBU, 46% 3 steps Ac 16 TBDPS 27 Ac 22 Me 1) 3 P, DIAD, ClC 2 C 2) DTC 3) TBDPSCl 51%, 3 stpes 4) MeMgBr 5) TPAP, M 69% 2 steps 1) PPTS 2) BF 3. Et 2 61% 3)Ac 2, pyr Prins Reaction 1) 2 PtCl 6 2) TBAF, 51% 2 steps 3) DMS, S 3. Py TBDPS R Ac C R=C=C 2 20 R=C 2 TBDPS Ac :1 17!/17" 1) SeBr 2) AIB, Bu 3 Sn 92%, 2 steps bromoetherification piperidine Ac 75% 2 steps 29 TBDPS Ac Ac C 1) TFA Me TBS 2) TBAF 51% 2 steps TBDPS 22 TBDPS CSA, 78% TFAT epimerization 5 LiCl 4 Tingting Wipf Group Page 6 of 9 /28/2009
7 8 Title paper: Synthesis of Eastern alf 31 P t-bu P P F E 22 P Eastern half 31 P P one anomeric effect kinetically controlled product P P two anomeric effect TBDPS Ac Ac 32 E 22 TBS remote oxidation trans-androsterone 34 + TMS 33 TBDPS TBS Ag 3, 2,6-lutidine 93%, 2 steps TBDPS PMP 35 1) TBDPSCl, imd 2) CA 3) TMSCl, imd 80% 3 steps TMS 1) DMS, (CCl) TBDPS 2 TMS TMS 2) TMSCC, Zn(Tf) 2 (+)--methylephedrine 57% 2 steps TMS 3) TBSCl, imd Carreira alkynylation 39 TBS Tingting Wipf Group Page 7 of 9 /28/2009
8 9 Title paper: Synthesis of Eastern alf 31 trans-androsterone 34 2 Ts 89% 40 Cu(Tf) 2, Et 3 benzoin, 2 25% " selective oxidation 41 1) Ac 2, pyr 2) (Tf) 2, KMDS 82% 2 steps Ac 43 Tf 33, Pd(P 3 ) 4 CuI, i-pr 2 Et 94% TBDPS TMS Ac 43 TBS 1) AD-mix!, 95% 2) (Se) 2, K 2 C 3 3) ab(ac) 3 36% 2 steps TBDPS TMS Ac 46 TBS 3 PAuCl AgBF 4 88% Au catalyzed cyclization TMS Ac TBDPS TBS 47 1) C 2 I 2, Et 3 2) PPTS 78% 2 steps Ac 32 TBDPS TBS BS Ac Ac 49 Br TBDPS TBS 1) Bu 3 Sn, AIB 2) TMSTf, pyr 65% 3 steps 3) KC 3 4) Cr4 88% 2 steps TMS Ac 31 TBDPS TBS Tingting Wipf Group Page 8 of 9 /28/2009
9 10 Completion of the synthesis of Cephalostatin 1 1) Me 3 Br ) tetramethylguanidinium azide 83% 2 steps 1) Me 3 Br 3 2) tetramethylguanidinium azide 78% 2 steps 3) 2 Me, pyr. 4) P 3, TF 77% 2 steps Au(I)-catalyzed 5-endo-dig cyclization 2 52 Me 56 A unique methyl group-selective allylic oxidation: 1) Bu 2 SnCl 2, polyvinylpyridine 2) TBAF 47% 2 steps 1 Tingting Wipf Group Page 9 of 9 /28/2009
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