Bioinspired Total Synthesis of Agelastatin A
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1 Bioinspired Total Synthesis of Agelastatin A Jeremy Chris P. Reyes and Daniel Romo Benjamin R. Eyer Wipf Group-Current Literature August 25, 2012 Angewandte Chemie International Edition. 2012, 51(28), DI: Benjamin /anie Wipf Group Page 1 of 13 8/31/2012
2 Agelastatins: Isolation and Bioactivity Tetracyclic pyrrole-2-aminoimidazole alkaloids (PAIs) isolated from axinellid sponges 1993: Agelastatin A and B isolated from Agelas dendromorpha 1998: Agelastatin C and D isolated from Cymbastela sp. 2010: Agelastatin E and F isolated from Agelas dendromorpha The molecular structures of all the agelastatin alkaloids and biogenetically related naturally occurring simpler pyrrole imidazole alkaloids Agelastatin A Most bioactive of PAIs ighly cytotoxic to human-cancer cell lines (IC 50 s nm) Potent inhibitor of osteopontin-mediated neoplastic transformation and metastasis Potentially antiangiogenic, antidiabetic, and insecticidal at. Prod. Rep. 2011, 28, J. Chem. Soc. Chem. Commun. 1993, J. at. Prod. 2010, 73, ncol. Res. 2005, 15, Mol. Cancer Benjamin Ther. Eyer Wipf 7, Group Chem. Biol. 2000, 7, Page 2 of 13 8/31/2012
3 Previous synthetic work on Agelastatin A 12 total syntheses to date C-ring has all 4 stereogenic centers in Agelastatin A Synthetic challenge Previous syntheses focused on the cyclopentane then late stage B and D ring construction Weinreb Feldman ale Davis Ichikawa Wardrop Chida Maruoka A All syntheses C D R B Trost Feldman Trost Wardrop Tanaka DuBois ale Movassaghi Maruoka Weinreb- JC 1998, 63,7594 and JACS 1999, 121, (1 st synthesis) Feldman- JACS 2002, 124, 9060 and JC 2002, 67, (1 st asymmetric synthesis) ale- L 2003, 5, 2927 and L 2004, 6, Davis- L 2005, 7, 621 and Syn. Comm. 2009, 39, (Wipf Group Current Lit. Feb. 2005) Trost- JACS 2006, 128, 6054 and Chem. Eur. J. 2009, 15, Ichikawa- L 2007, 9, Wardrop- L 2009, 11, Chida- L 2009, 11, Tanaka- L 2008, 10, 5457 and L 2009, 11, DuBois- ACIE 2009, 48, (Wipf Group Current Lit. May 2009) Movassaghi- Chem. Sci. 2010, 1, 561. (Wipf Group Current Lit. Aug. 2010) Maruoka- JACS 2012, 134, Benjamin Wipf Group Page 3 of 13 8/31/2012
4 Proposed biogenetic synthesis of roidin-based pyrrole-imidazole alkaloids ACIE. Benjamin 2012, 51(28), Wipf Group Page 4 of 13 8/31/2012 Eur. J. rg. Chem. 2001,
5 Movassaghi s biosynthetic approach: B-ring then C-ring Me Me ClS 2 C, MeC; a(g), a 2 P 4 82% 2 Me Me ab 4,Me; Ts, 2 Me Me Me >10 g scale 90%, 99% ee 3 steps 2 : 1 MeS 3, 2, 100 o C; Me 66% Me MeS 3, 2, 100 o C; Me 71% >1 g scale Me Benjamin Wipf Group Page 5 of 13 8/31/2012 Chem. Sci. 2010, 1,
6 Title Paper s bioinspired approach: C-ring then B-ring R 2 nagelamide J 2 keramadine R= 2 A D C R B Agelastatin A C-ring then B-ring formation hydration Et R Et Proposed bioinspired cascade cyclizations Et R Me R or R R Tetrahedron Lett. 2000, 41, rg. Lett. Benjamin 2007, Eyer 9, 2369 Wipf Group Page 6 of 13 8/31/2012
7 Synthesis of the Coupling Partners 2 C 2 C Me 2 2 S 4 80 o C 54% 2 C 1. K 2 C 3, MeI, then K 2 C 3 TseMs,DMF,60 o C 2. DIBAL-, DCM, -78 o C 3. Mn 2, DCM, 23 o C 85%, 3 steps C Tse ame, Me/C 2 Cl 2 Me P -40 o Cto23 o C Me 56% 2 Et Tse ZnI 2, C(Et) o C 84% Tse Et CCl 3 2 Me Cl Et 3,80 o C 98% Me BS TF/Me 95% Me Benjamin Wipf Group Page 7 of 13 8/31/2012
8 Coupling of imidazolone alkynyl acetal and pyrrole amide Benjamin Wipf Group Page 8 of 13 8/31/2012
9 Biomimetic C-Ring Closure Single diastereomer Addition of a variety of Lewis and ønsted acids resulted in deer-red colored solution Benjamin Wipf Group Page 9 of 13 8/31/2012
10 Probing the Reaction Mechanism Experimental vs TD-DFT predicted absorption bands Benjamin Wipf Group Page 10 of 13 8/31/2012
11 Completion of Synthesis: Closing the B-Ring Tse group removed to allow greater confirmational mobility 4,5-bis-epi-agelastatin formed by retro-azarov reaction (retro-5-exo-trig) then recyclization Absence of the Tse group, the C5 unprotected alcohol and the C13 bromine in the pyrrole ring essential to cyclization Benjamin Wipf Group Page 11 of 13 8/31/2012
12 Enantioselective azarov-type Cyclization Preliminary Studies with (R)-TRIP hydrogen phosphate show promise for an enantioselective route and further studies are currently underway Benjamin Wipf Group Page 12 of 13 8/31/2012
13 Summary Concise total synthesis of agelastatin A that complements Movassaghi s approach to the agelastatins (B-ring then C-ring) Completion of the total synthesis by two sequential, potentially biomimetic cyclizations (C-ring then B-ring) C-ring: sets three contiguous centers diastereoselectively B-ring: unique solvent-free conditions on silica gel with mild heating Proposal for the biosynthesis of the agelastatins through a reaction sequence leading from an oxidized keramadine analogue via a nagelamide J like intermediate to agelastatin A The assembly of C followed by B rings provides evidence for the proposed reactivity of a linear alkenyl imidazolone pyrrole R 2 nagelamide J 2 keramadine 2 cyclooroidin A D C R B agelastatin A R= 2 Benjamin Wipf Group Page 13 of 13 8/31/2012
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