I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, and P. S. Baran, Angew. Chem. Int. Ed. 2009, 49,
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1 I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, and P. S. Baran, Angew. Chem. Int. Ed. 09, 49, ong The Wulff Group
2 2 2 2 Synthesized naturally by Stylotella agminata Cytotoxic and immunosuppressive In 993, first isolated by P. J. Scheur and co-workers In 07, structure revision proposed by M. Kock 2 Ph. D theses and 3 publications In 09, first total synthesis accomplished by P. Baran Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
3 2 2 2 Synthesized naturally by Stylotella agminata Cytotoxic and immunosuppressive In 993, first isolated by P. J. Scheur and co-workers In 07, structure revision proposed by M. Kock 2 Ph. D theses and 3 publications In 09, first total synthesis accomplished by P. Baran Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
4 2 2 ine nitrogens 2 Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
5 2 2 ine nitrogens 2 Eight contiguous stereogenic centers Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
6 2 2 ine nitrogens 2 Eight contiguous stereogenic centers Reactive (hemi)aminal moieties Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
7 2 2 ine nitrogens 2 Eight contiguous stereogenic centers Reactive (hemi)aminal moieties ighly polar bis-guanidines Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
8 2 2 ine nitrogens 2 Eight contiguous stereogenic centers Reactive (hemi)aminal moieties ighly polar bis-guanidines xidation-prone pyrroles Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
9 2 2 ine nitrogens 2 Eight contiguous stereogenic centers Reactive (hemi)aminal moieties ighly polar bis-guanidines xidation-prone pyrroles Strained trans fused 5,5 - azabicyclic ring Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
10 2 2 ine nitrogens 2 Eight contiguous stereogenic centers Reactive (hemi)aminal moieties ighly polar bis-guanidines xidation-prone pyrroles Strained trans fused 5,5 - azabicyclic ring Unprecedented hexacyclic core Kock, M.; Grube, A.; Seiple, I. B.; Baran, P. S. Angew. Chem. Int. Ed. 07, 4,
11 transannular closure amidine tautomer 2 2 tautomerization Br 2 S Ar amide formation macro- 2 I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, and P. S. Baran, Angew. Chem. Int. Ed. 09, 49,
12 Et Et + BF 3 Et 2 0 C then RT Et Et Et C/ Ca 2, 0 C C TIPSTf Et 3, 0 C Me Me 2 C C 2 Me Me C 2 Me. LA 2. Ms Me 3 Me TIPS Me TIPS C 2 Me 3. a 3 4. TBAF 4% Me Yamaguchi, J.; Grube, A.; Seiple, I. B.; Young, I. S.; Baran, P. S. Angew. Chem. Int. Ed. 08, 47, Gosselin, P.; Bourdy, C.; Mille, S.; Perrotin, A. J. rg.chem. 999, 4,
13 Me 3. PMB 2. 3 Me 3. TMSTf i Pr 2 Et then BS 3 3 Me % PMB 8 3 Me 2. Si 2 57% PMB 9 Br Br. Li 2. TFA 3 3. S 2 2 2,-lutidine % Br 38-43% Br Yamaguchi, J.; Grube, A.; Seiple, I. B.; Young, I. S.; Baran, P. S. Angew. Chem. Int. Ed. 08, 47,
14 3 3 Br 3 ab 4 Ce Br 2 2 Boc Boc DBU 55% 3 Boc Boc IBX 3 a(c) %, dr =.3: I 72% Boc Boc Boc Boc 4 5 (C) 2 IBX Yamaguchi, J.; Grube, A.; Seiple, I. B.; Young, I. S.; Baran, P. S. Angew. Chem. Int. Ed. 08, 47,
15 3 3 Boc Boc 5 (C) 2 50% aq. TFA then aq % TFA Ag 4% C brine 5% I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, and P. S. Baran, Angew. Chem. Int. Ed. 09, 49,
16 TFAA/TFA then Br 2 54% Br 2 2 tbu 2 C Me Me Me Me Me tbu 2 C Me then TFA Me tbu 2 C Me 2 9 I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, and P. S. Baran, Angew. Chem. Int. Ed. 09, 49,
17 3 3 2 Me tbu 2 C Me -2Me C 44% 2 2, Pd(Ac) C 2 2 EDC, Bt macro- 2 I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, and P. S. Baran, Angew. Chem. Int. Ed. 09, 49,
18 macro- then TFA 70 C macro % 2 I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, and P. S. Baran, Angew. Chem. Int. Ed. 09, 49,
19 25 steps, 0.05% overall yield Multiple cascade reactions Minimal use of protection groups: PMB Late-stage, chemoselective, silver-mediated oxidation to the hemiaminal unit then aq % TFA Ag %
20 The ambiphilic reactivity of 2-aminoimidazole TFAA/TFA then Br 2 54% E 3 3 uc 2 Br macro- Across ring stitching 9
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