Total Synthesis of (+)-Sieboldine A J. Am. Chem. Soc. 2010, 132,
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1 Total Synthesis of (+)-Sieboldine A J. Am. Chem. Soc. 2010, 132, Current Literature Presentation 10JUL2010 Michael Yang Mike Wipf Group Page 1 of 15 7/10/2010
![1 μg/ml) Alopecuridine may be the biosynthetic precursor of Sieboldine A Alopecuridine [] [] [] []](/docs-images/81/84372250/images/2-1.jpg "[] irasawa Y.; Morita,.; Shiro, M.; Kobayashi, J. rg. Lett. 2003, 5, 3991-3993.")
2 Sieboldine A Background Isolated from club Moss Lycopodium sieboldii Inhibition of acetylcholinesterase (IC μg/ml) Cytotoxicity against murine lymphoma L1210 cells (IC μg/ml) Alopecuridine may be the biosynthetic precursor of Sieboldine A Alopecuridine [] [] [] [] [] irasawa Y.; Morita,.; Shiro, M.; Kobayashi, J. rg. Lett. 2003, 5, Mike Wipf Group Page 2 of 15 7/10/2010
3 Retrosynthetic Analysis R R R pinacol-terminated cyclization TES + I Y SiR 3 Y Key Step: -terminated Cyclization TES LA TBDPS TES LA TBDPS TBDPS Canham, S. M.; France, D. J.; verman, L. E. J. Am. Chem. Soc. 2010, 132, Mike Wipf Group Page 3 of 15 7/10/2010
4 -terminated Cyclization (xacyclic Ring Systems) Tetrahydrofuran Synthesis Ring-expansion C 2 Et SnCl % exahydroisobenzofuran BF + 3 Et 2 C 2 Cl 2 65% C 2 Et 2 C SnCl % Ac Tetrahydropyran Synthesis i-prc SnCl % i-pr i-pr i-pr verman, L. E.; Pennington, L. D. J. rg. Chem. 2003, 68, Mike Wipf Group Page 4 of 15 7/10/2010
5 -terminated Cyclization (Carbocyclic Ring Systems) Cyclopentane Synthesis TMS Et 1) SnCl 4, C 2 Cl 2-78 C 2) Ru 4, C/ 2 62%, 2 steps Et TMS Et TMS Et Ring Expansions TMS C() 2 SnCl 4, -78 C to -23 C C 2 Cl 2 68% TMS TMS TBDMS C() 2 SnCl 4, -70 C to -23 C C 2 Cl 2 80% TBDMS TBDMS Ring Contraction TIPS SnCl 4, 0 C 2 75% TIPS C verman, L. E.; Pennington, L. D. J. rg. Chem. 2003, 68, Mike Wipf Group Page 5 of 15 7/10/2010
6 -terminated Cyclizations Alternative Cationic Initiators Allyl cation as cyclization initiator TES TMS Tf TMS TMS 2 TMS TMS C 2 Cl 2, -78 C 80% Keteniminium ion as cyclization initiator TES Tf 2 DCE, -78 C to -20 C 72% TMS TMS verman, L. E.; Wolfe, J. P. J. rg. Chem. 2002, 67, Mike Wipf Group Page 6 of 15 7/10/2010
7 - to Form xacyclic Core of Briarellin E TIPS + TBDPS C p-ts 2, MgS 4, C 2 Cl 2, -78 C to -20 C TIPS TMS SnCl 4, C 2 Cl 2, -78 C to RT 84%, 2 steps TMS TBDPS TMS TIPS TMS C TIPS TBDPS TBDPS TIPS TMS TBDPS Briarellin E C 2 C 7 15 Corminboeuf,.; verman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2003, 125, Mike Wipf Group Page 7 of 15 7/10/2010
8 - to Form Carbocyclic Core of Magellanine and Shahamin K Et 3 Si SnCl 4, 78 C to 23 C C 2 Cl 2 57% Et 3 Si Magellanine Ac TMS C(S) 2 DMTSF C 2 Cl 2, -45 C 80% TMS S S Ac Shahamin K irst, G. C.; Johnson, T..; verman, L. E. J. Am. Chem. Soc. 1993, 115, Lebsack, A. D.; verman, L. E.; Valentekovich, R. J. J. Am. Chem. Soc. 2001, 123, Mike Wipf Group Page 8 of 15 7/10/2010
9 Preparation of Chiral Cyclopentanone TBDPS TES Ac (allylpdcl) 2 Cs 2 C 3, A C 2 Cl 2 91% yield, 96% ee C 2 C 2 1) acl, 2, DMS, 160 C, 81% 2) aq. K,, TF 60 C, 95% C 2 1) KI, I 2, ac 3 TF, 2 90% 2) DBU, 96% 1) MgBr, CuBr S 2 LiAl 4, 2) KI, I 2, ac 3 83% 93% I 1) TESCl, 2,6-lutidine, 98% 2) DMP, 97% TES P 2 2 P A Trost, B. M.; Bunt, R. C. Angew. Chem. Int. Ed. 1996, 35, Miyazaki, T.; Yokoshima, S.; Simizu, S.; sada,.; Tokuyama,.; Fukuyama, T. rg. Lett. 2007, 9, Canham, S. M.; France, D. J.; verman, L. E. J. Am. Chem. Soc. 2010, 132, Mike Wipf Group Page 9 of 15 7/10/2010
10 Preparation of Precursor 1) TBDPSCl, imid. 97% 2) n-buli, ClC 2, 95% C 2 TBDPS Bu 3 Sn, LDA, CuBr S 2, TF, 78 C; 93% Bu 3 Sn C 2 TBDPS 1) DIBAL-, 99% 2), P 3, DIAD, 90% 3) I 2, 82% I B TBDPS TES s-buli, B, TF -78 C CeCl 3 2LiCl TES TBDPS 1) TESCl, 2,6-lutidine, 90% 2) Swern, 86% 3) TBDPS 90% P() 2 TES 2 K 2 C 3,, 90% Delongchamps, P.; all, D. G. J. rg. Chem. 1995, 60, Canham, S. M.; France, D. J.; verman, L. E. J. Am. Chem. Soc. 2010, 132, Mike Wipf Group Page 10 of 15 7/10/2010
11 -terminated Cyclizations TBDPS TES -terminated cyclization TES TBDPS Lewis acid <45% TBDPS -terminated enyne cyclization Au TES TBDPS (t-bu) 2 P(o-biphenyl)AuCl, AgSbF 6, i-pr, C 2 Cl 2 78% TES TBDPS TBDPS Canham, S. M.; France, D. J.; verman, L. E. J. Am. Chem. Soc. 2010, 132, Mike Wipf Group Page 11 of 15 7/10/2010
12 Divergent reactivity of 3-Siloxy 1,6 Enynes R 2 R 3 SiR 3 R 1 M R 2 R 3 SiR 3 R 1 M SiR 3 AgSbF R 2 6, i-pr, C 2 Cl 2 R 3 81%(19:1) 83% (8:1) R 1 pinacol rearrangement (t-bu) 2 P(o-biphenyl)AuCl M AuClP(C 6 F 5 ) 3 R 3 Si AgSbF 6, i-pr, C 2 Cl 2 R 2 R 3 R 1 M [3,3] sigmatropic rearrangement R 2 R 3 R 1 R 1 R 2 R 3 R 3 Si R 3 R 2 R 1 M Baskar, B.; Bae,. J.; An, S. E.; Cheong, J. Y.; Rhee, Y..; Duscheck, A.; Kirsch, S. F. rg. Lett. 2008, 10, Mike Wipf Group Page 12 of 15 7/10/2010
13 Formation of TF ring TBDPS 1) 3 ; 2 S 2) DBU 75% TBDPS Eu(fod) 3, ethyl vinyl ether 86% Et TBDPS DIBAL- Et 1) DMD 2) BF 3 Et 2, EtS 53% (3 steps) SEt TBDPS TBDPS DMD Et SEt TBDPS TBDPS Canham, S. M.; France, D. J.; verman, L. E. J. Am. Chem. Soc. 2010, 132, Mike Wipf Group Page 13 of 15 7/10/2010
14 Endgame SEt 1) TBAF, 91% 2) s-mm, P 3, DEAD, 88% 3) S, K 2 C 3, 95% SEt DMTST, DTBMP, 4A MS, 88% TBDPS MM MM 1) TPAP, M, 88% 2) 2 BBr, 67% (+)-Sieboldine A Canham, S. M.; France, D. J.; verman, L. E. J. Am. Chem. Soc. 2010, 132, Mike Wipf Group Page 14 of 15 7/10/2010
15 Summary -terminated cyclizaion have been used to form the oxacyclic and carbocyclic core of many alkaloid. Alternative cationic initiators can be used: Gold-catalyzed enyne cyclization used in Sieboldine A. Sieboldine A prepared in 27 linear steps from commercially available material (33 overall). Mike Wipf Group Page 15 of 15 7/10/2010
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