Nilson, M. G.; Funk, R. L. Org. Lett. 2010, ASAP. Chad Hopkins Wipf Group Literature Presentation
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1 TtlS Total Synthesis of ( ) akadomarin kd A ilson, M. G.; Funk, R. L. rg. Lett. 2010, ASAP. Chad opkins Wipf Group Literature Presentation Chad Wipf Group Page 1 of 11 12/5/2010
2 Isolation and Biological Activity ( ) akadomarin A Isolated in 1997 from the marine sponge Amphimedon sp. collected off the coast of the Kerama Islands, kinawa (1 kg of sponge yielded 6.0 mg or % of ( ) akadomarin A). Structure assigned by 1 D/2 D MR, RMS (EI), and Macromodel (v 5.0, Pseudo Monte Carlo, MM2 FF 2 ) ovel furan conatining hexacyclic alkaloid consisting of an unprecedented 8/5/5/5/15/6 ring system Cytotoxic against murine L1210 (mouse lymphoma, IC µg/ml or 3.5 µm) Demonstrated ant fungal and anti bacterial activity First asymmetric synthesis completed in 2004 by ishida Kobayashi, J.; Watanabe, D.; Kawasaki,.; Tsuda, M. J. rg. Chem. 1997, 62, no, K.; akagawa, M.; ishida, A. Angew. Chem. Int. Ed. 2004, 43, Chad Wipf Group Page 2 of 11 12/5/2010
3 First Synthesis of (+) akadomarin (ishida) 19 steps Bs C 2 10% yield 6 steps from comm. material Bs Ac Ac Boc TP " + " 2 steps 87% yield Bs Ac Boc 8 steps 21% yield RCM 70% yield (E / Z : 1.7 : 1.0) Reduction 86% (+)-akadomarin Longest Linear Sequence: 31 steps from chiral acid, 1.1% 11%yield agata, T.; akagawa, M.; ishida, A. J. Am. Chem. Soc. 2003, 125, For ishida s synthesis of ( ) akadomarin, see: no, K.; akagawa, M.; ishida, A. Angew. Chem. Int. Ed. 2004, 43, For Kerr s synthesis of (+) akadomarin, see: Young, I. S.; Kerr, M. A. J. Am. Chem. Soc. 2007, 129, Kerr s Longest Linear Sequence: 29 steps from D mannitol, RCM for 15 membered ring gave a E : Z = 1.5 : 1.0 Chad Wipf Group Page 3 of 11 12/5/2010
4 Synthesis of ( ) akadomarin (Dixon) Jakubec, P.; Cockfield, D. M.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, Longest Linear Sequence: 12 steps, 1.4% yield Chad Wipf Group Page 4 of 11 12/5/2010
5 Vicinal Difunctionalization For a review on tandem vicinal difunctionalization involving acyliminium ions, see: Maryanoff, B. E.; Zhang,. C.; Cohen, J..; Turchi, T. J.; Marynoff, C. A. Chem. Rev. 2004, 104, For a review on tandem vicinal difunctionalization involving α,β unsaturated carbonyls, see: Chapdelaine, M. J.; ulce, M. rg. React. 1990, 38, Inter Intra Suga. S.; ishida, T.; Yamada, D.; agaki, A.; Yoshida, J. I. J. Am. Chem. Soc. 2004, 126, Tamura, Y.; Maeda,.; Akal, S.; Ishibashi,. Tetrahedron Lett. 1982, 23, Padwa, A.; Danca, M. D.; ardcastle, K. I.; McClure, M. S. J. rg. Chem. 2003, 68, For a review on tandem vicinal difunctionalization involving acyliminium ions, see: Maryanoff, B. E.; Zhang,. C.; Cohen, J..; Turchi, T. J.; Marynoff, C. A. Chem. Rev. 2004, 104, Chad Wipf Group Page 5 of 11 12/5/2010
6 Method Development Towards Core of ( ) akadamarin (Funk) Me 2 C 2 C Me 2 C C 2 Me C 2 Me C 2 Me Yb(Tf) 3 a i-buccl i-bu MeC, 40 o C TF 90% 89% 99% C 2 Me Boc DCM, 0 o C 50% Boc Z-unsaturated amide ilson, M. G.; Funk, R. L. rg. Lett. 2006, 8, C 2 Me Sc(Tf) 3 (0.1 equiv) DCM, 0 o C 33% (addition of 2.0 equiv of 2 improved yield to 54%) Me 2 C Boc 1:2( separable ab e PCC DCM : 59% : 42% Me 2 C o furan trapping of acyliminium ion observed, cis vs. trans Boc X Ray of β hemiaminal Chad Wipf Group Page 6 of 11 12/5/2010
7 Method Development Towards Core of ( ) akadamarin (Funk) X Ray of tetracycle ilson, M. G.; Funk, R. L. rg. Lett. 2006, 8, Chad Wipf Group Page 7 of 11 12/5/2010
8 Retrosynthesis of ( ) akadamarin (Funk) ilson, M. G.; Funk, R. L. rg. Lett. 2010, ASAP. Chad Wipf Group Page 8 of 11 12/5/2010
9 2 C D-Pyroglutamic acid 4steps 67% yield Synthesis of ( ) akadamarin (Funk) TIPS Boc C LiBEt 3 i-pr 2 Et, DMAP (CCl) 2 TFAA 88% TIPS Boc DMF 87% TIPS Boc 1) then ab 4 2 C 2 Me 2) Cl Me TIPS Boc 66% (2 steps) ilson, M. G.; Funk, R. L. rg. Lett. 2010, ASAP. Chad Wipf Group Page 9 of 11 12/5/2010
10 Synthesis of ( ) akadamarin (Funk) ilson, M. G.; Funk, R. L. rg. Lett. 2010, ASAP. Chad Wipf Group Page 10 of 11 12/5/2010
11 End Game and Summary Enantioselective synthesis of ( ) akadomarin 21 steps (LLS), 3.5% overall yield from D pyroglutamic acid ighest overall yielding synthesis to date Rapid assembly of tetracyclic core via a tandem enecarbamate Michael addition/furan acyliminium ion cyclization RCAM resolves olefin stereoselectivity issues with construction of 15 membered ring Cyclization of pyrrole analog of furan successful ilson, M. G.; Funk, R. L. rg. Lett. 2010, ASAP. Chad Wipf Group Page 11 of 11 12/5/2010
Total Synthesis of ( )-Nakadomarin A
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