Stereoretentive Suzuki-Muyaura Coupling of Haloallenes Enables Fully Stereocontrolled Access to ( )-Peridinin
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1 Stereoretentive Suzuki-Muyaura Coupling of aloallenes Enables Fully Stereocontrolled Access to ( )-Peridinin 3' ' ' 5' 5 5 Ac Eric M. Woerly, Alan. Cherney, Erin K. Davis and Martin D. Burke J. Am. Chem. Soc. (ASAP) Current Literature May, oo Sammi Wipf Group Page of 5/3/00
2 solation and Structural Features: solated in 890 by Schütt from fresh-water dinoflagelletes (causing red-tide, > 0 6 cells/ml). Later isolated from corals, clams and sea anemones. Dinoflagelletes - red pigment important for photosynthesis. Full structure and assignment of Peridinin wasn t achieved till 97. nteresting features: Ac (+)-Peridinin (Z)-γ-ylidenebutenolide moiety (anticancer activity?) C37 nor-carotnoide Stereogenic allene. More recently, Peridinin suggested as quencher; associated with atherosclerosis rheumatoid arthritis and cancer, contributing to the aging process. st Total synthesis of (±)-Perdinin was completed over 00 years later by to (993), confirmed the structure. Schütt, F. Ber. Deut. Bot. Ges. 890, 8, 9. Lieean-Jensen, S. at al J. Am. Chem. Soc. 97, 93, 83 Johansen, J. E.; Borch, G.; Liaaen-Jensen, S. Phytochemistry 980, 9, 44 Yamano, Y.; Tode, C.; to, M. J. Chem. Soc. Perkin Trans. 993, 599. Sammi Wipf Group Page of 5/3/00
3 Katsumra s Total Synthesis: Ac 5 5 5' 3' 0' C ' Ac TBS 4 5 P + Ph 3 - TBS C Me 6a 3 6b 4. 5, nbuli, 3 h. TPP,, hv,!78 o C 77%, steps TBS. ipr Et, DMS, 3h, r.t. then Allyl, r.t., h, 70%. C 4, PPh 3, Et 3,! 60 o C, h, 89% 3. TBAF, 8% Allyl 6b, (Ph 3 P) 4, Et 3, Cu, r.t. h then C, 0 h, 49%. Mn, Et, 3h. ClC P + Ph 3 Cl -, nbuli. 6a, (Ph 3 P) 4, ipr,. Ac, pyr,! 30 o C, 3h Cu, r.t. h, 84% 86%, steps 4. tbuk, DMS, r.t, 0 min 53%, steps. DBAl, 0 o C, 80% 3. ab 4, Me, 98% 3 Sonogashira Coupling ed. Elimination 3 ' ' Ligand Exchange Al ' nsertion ' Domino eaction Furuichi,.; ara,.; saki, T.; akano, M.; Mori,.; Katsumura, S. J. rg. Chem. 004, 69, Yamano, Y.; Tode, C.; to, M. J. Chem. Soc. Perkin Trans. 993, 599. Sammi Wipf Group Page 3 of 5/3/00
4 Katsumra s Total Synthesis cont.. 7, DAD. PPh 3, 78%. ( 4 ) 6 Mo 7 4, aq, 89% S 3 S 7 Mn Et C Ac S S amds!78 o C dark, 5 min Ac E/Z /3 Benzene r.t. 3 d E/Z > 5/ 50% from aldehyde Ac C33 Ac C35 Ac C39 Peridinin posses large static dipole moment facilitating energy transfer. Katsumura at el rg. Lett. 009,, Sammi Wipf Group Page 4 of 5/3/00
5 ückner s Approach to the Butenolide Moeity: Me C Me C Bu 3 Sn + C Et C Et (!)-diethyl tartrate C 4 4-deoxy-4 Me C Me C 4. Et C C Et 3 steps. ab 4 (8.0 eqv), 98% Me C Me. Swern [], 90% Me C Me 3. a, TF, 90% E:Z =95:5 Ph P Ph C Et C Et Amberlyst 5, Me reflux, 8 h, 95% Me C. 3, Me. ab 4 C 3. Sharpless, 67%, 99.8%ee 4. Swern [], 99%. LDA, TMSC. Bu 3 Sn, (PPh 3 ) 4 Bu 3 Sn + Me C. Cu, dba 3, P(-furyl) 3, 84%. DEAD, Ph 3 P,! 30 o C, 5% was also prepared in the same fashion. Later in 006, used the same methodology to complete the synthesis of Peridinin. lpp, T.; ückner,. Angew. Chem., nt. Ed. 005, 44, lpp, T.; ückner,. Angew. Chem., nt. Ed. 006, 45, 403. Sammi Wipf Group Page 5 of 5/3/00
6 Burke s Work: MDA Mask ighly unreactive. Very stable to most C-C conditions. Easily removable under mild conditions. Stable to silica chromatography and storage. Me Me Crocacin C Me Me SnBu 3 3 B 4 B. Me 3 BF 4, proton sponge, 8%. CA, 77% Me Me PMB B B. DMP, 97%. C 3, CrCl TF:Dioxane, 74% 3, (PPh 3 ) 4 Cu, CsF, DMF 6% Me Me B ine linear steps synthesis of crocacin C 4, (Ac) SPhos, K 3 P 4 77% Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 007, 9, 676. Gillis, E. P.; Burke, M. D. J. Am. Chem. Soc. 008, 30, Sammi Wipf Group Page 6 of 5/3/00
7 Title Paper - Key eaction: Stereoretentive SM cross-coupling Ac terative Cross Coupling (CC) TBS B B B 3 B TMS B B B 4 Ac Key eaction: () X PhB(), Ag (dba) 3, Ligand TF:, rt,.5 h () Ph C C C X PhZn or PhZnCl cat. (PPh 3 ) 4 C C C Ph Woerly, E. M.; Cherney, A..; Davis, E. K.; Burke, M. D. J. Am. Chem. Soc. (ASAP) Elsevier, C. J.; Vermeer, P. J. rg. Chem. 985, 50, 304. Sammi Wipf Group Page 7 of 5/3/00
8 (0)-Catalysed Phenylation of -aloallenes: () X nversion X = Cl or etention X = Ph Ph L 4 nversion: C C C Ph L C C C X X L!L etention: () (PPh 3 ) 4 L halide transfer X S ' anti L L (retention) L X [,3]-shift xidative addition to decreases > > Cl, as in vinyl halides. eavier metals, group V show affinity to heavy halogens. Possible radical intermediate in which recombination rate is faster. C C C cage L L () L L X Ph L L X C C C L C C C L ZnXY PhZnY Proposed catalytic cycle Elsevier, C. J.; Vermeer, P. J. rg. Chem. 985, 50, 304. Sammi Wipf Group Page 8 of 5/3/00
9 Application in Synthesis: Lera s Synthesis of Peridinin:. Cu, 4, Et, 85%. Ac, pyr, 85% Ac Bu 3 Sn [(PhC) Cl ], S BT ( i Pr) Et, DMF:TF 64% Ac 6' S BT 6'-epi-Peridinin Ac X xidative addition L X Ac Transmatalation then eductive Elimination Product with etention "L " anti-s ' displacement of L X superfacial,3-shift L X Transmatalation then eductive Elimination Product with nversion Ac aloallene atural Products: Ms LiCu Panacene Laurellene Vaz, B.; Domínguez, M.; Alvarez,.; de Lera, A.. Chem.-Eur. J. 007, 3, 73. K. S. Feldman, C. C. Mechem, L. ader, J. Am. Chem. Soc. 98, 04, 40. M. T. Crimmins, E. A. Tabot, J. Am. Chem. Soc. 000,, Sammi Wipf Group Page 9 of 5/3/00
10 Title Paper: Forward Synthesis Stereoretentive SM cross-coupling terative Cross Coupling (CC) Ac TBS B B B B B 3 B TMS Ac B 4 TBS pinb Cy B 8% TBS B C Me C DMS, 3 cycles 73% TBS B B B Bu 3 Sn Mo. cat TF 84% Bu 3 Sn B, (dba) 3, Ph 3 As TF 77% B B Mo cat = [Mo(allyl)(C) (C 3 C) ] Structure confirmed by X-ray Woerly, E. M.; Cherney, A..; Davis, E. K.; Burke, M. D. J. Am. Chem. Soc. (ASAP) Furuichi,.; ara,.; saki, T.; akano, M.; Mori,.; Katsumura, S. J. rg. Chem. 004, 69, Zhang,. X.; Guibe, F.; Balavoine, G. J. rg. Chem. 990, 55, 857. Sammi Wipf Group Page 0 of 5/3/00
11 Total Synthesis of (-)-Peridinin: Final Steps B., C Cl. DBU, MeC 67% B., Cl (PPh 3 ), DMF:TF, 74%., Me, 77% B., (PPh 3 ) 4, CuTc, DMF, 58%., Me, 75% B 3 B Et 3 Ge SnBu 3 TBS B. a, TF:, 95%. B, (Ac), XPhos, K 3 P 4, Tol:TF, 79% TBS B. pinacol, ac 3, Me, 99%. B 3, Cl (PPh 3 ), Ag, DMS, 45% B B TBS B. B 4, (Ac), XPhos, a, TF:, 60%. F.pyr, TF, 65% TMS (-)-Peridinin Ac Ac B 4 i Pr PCy i Pr = XPhos i Pr Woerly, E. M.; Cherney, A..; Davis, E. K.; Burke, M. D. J. Am. Chem. Soc. (ASAP) Sammi Wipf Group Page of 5/3/00
12 Conclusion: Synthesis of (+)-Peridinin focused on a late stage construction of olefins, which proved problematic due to the E/Z isomerization. Burke s strategy proved successful in avoiding the isomerization using a different approach, SM cross coupling, in his synthesis of (-)-Peridinin. Combination of bulky substituent and ligand promoted stereoretention in SM cross coupling of odo-allenes. Using a more stable MDA boronates which has a lot of advantageous in the modern synthetic chemistry. Achieved st Stereoselective total synthesis of ( )-Peridinin. Sammi Wipf Group Page of 5/3/00
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