Synthetic Efforts Toward Palau'amine
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1 ynthetic Efforts Toward Palau'amine Doug Behenna, Ryan McFadden Eric Ashley, Jenn tockdill Akihiko Iwashita August 9, Isolation of Palau'amine and Congeners R 2 R 1 R 1 R R 1 = R 2 = Palau'amine R 1 =, R 2 = 4-omo Palau'amine R 1 = R 2 = Dibromo Palau'amine Palau'amines Isolated from marine sponge tylotella aurantium tructural determination by 1 MR Cytotoxic against P-388 (0.1 µg/ml), A549 (0.2 µg/ml), T-29 (2µg/mL) and KB (10 µg/ml) Antibiotic against taphylococcus aureus and Bacillus subtillus Antifungal against Penicillium notatum Kinnel, R. B. et. al. J. Am. Chem. oc. 1993, 115, and J. rg. Chem. 1998, 63, R 1 = R 2 = tyloguanidine R 1 =, R 2 = 3-omo tyloguanidine R 1 = R 2 = Dibromo tyloguanidine tyloguanidines Isolated from marine sponge tylotella aurantium tructural determination by 1 MR All three compounds are potent chitinase inhibitors First reported by Kato, T. et. al. Tetrahedron Lett. 1995, 36, Also reported in Kinnel's second paper. 1
2 Biosynthesis of Palau'amine 2 istidine C C 2 C 2 C 2 Proline C 2 2 Mourabit, A. A.; Potier, P. Eur. J. rg. Chem., 2001, Biosynthesis of Palau'amine
3 Biosynthesis of Palau'amine [] Palau'amine 2 verman's tereocontrolled ynthesis of the Tetracyclic Palau'amine Core CEt 1. 2 C 2 C 2 a, Et, reflux ,Et, reflux 3. Cbz, TEA Et 2 C Et 2 C Cbz 1. t-buk, TF, -78 o C 2. ab 4, Me Et 2 C Cbz Et 2 C Cbz Et 2 C Cbz 1. Ms, TEA, DMAP, Ph, 0 o C 2. 3, C 2 2 ; PPh 3 CsF, Ac, AC 3. Li, AC, (Me)PC(TB)C 2 Me Me 2 C TB Me 2 C verman, L.E. et. al., J. Am. Chem. oc. 1997, 119,
4 verman's tereocontrolled ynthesis of the Tetracyclic Palau'amine Core Et 2 C Cbz Me 2 C 2 C 2 Ac, 70 o C, 24h Cbz Et 2 C C 2 Me C 2 Cbz Et 2 C C 2 Me - + Cbz Et 2 C 2 C 2 Me Cbz C 2 Me 2 verman, L.E. et. al., J. Am. Chem. oc. 1997, 119, verman's tereocontrolled ynthesis of the Tetracyclic Palau'amine Core Cbz C 2Me Li, Cbz C 2 P(C) 3 TF, reflux Cbz MeI, a 2 /Me, RT Cbz 2, Et, 70 o C Cbz Me Me verman, L.E. et. al., J. Am. Chem. oc. 1997, 119,
5 ynthesis of Epimeric Cyclization Precursores E e 2, t-bu 2 C 2 2, reflux E acetone, PPT 20% Et 2 C (56% recovered 1) 1 largely (~90%) one stereoisomer Et 2 C 2 Me 2 C(Me) 2 E column chromatography E E Et 2 C Et 2 C Et 2 C 3 4a, 50-55% 4b, 15-20% L. E. verman et al. J. rg. Chem. 2002, 67, ynthesis of Epimeric Cyclization Precursores Dowex (resin) Me, rt E Et 2 C TBDM-Tf, Et 3, 0 C TBDM E Et 2 C 1. Ms 2. 3, PPh 3 3. (Me) 2 PC(TBDM)C 2 Me Li, DBU 5a:!- (74%) 5b: "- (80%) TBDM TBDM C 2 Et 6a:!-TBDM (75%) 6b: "-TBDM (48%) TBDM C 2 Et E Et 2 C 7a:!-TBDM (~35%) 7b: "-TBDM (~12%) CsF, Ac E MeC Et 2 C ~100% 8a:!-TBDM 8b: "-TBDM L. E. verman et al. J. rg. Chem. 2002, 67,
6 Intramolecular Cycloaddition Reactions E Et 2 C E Et 2 C TBDM C 2 Me 2 2 Ac, 70 C E 89% a:!-TBDM 9b: "-TBDM C 2 Me Ac, 70 C 2 2 E C 2Me TBDM C 2Me 12a:!-TBDM (49%) 12b: "-TBDM (58%) L. E. verman et al. J. rg. Chem. 2002, 67, ,2:5,6-di--isopropylidene- D-mannitol $$$ The Pauson-Khand Approach ai 4, ac 3 4:1 Me/ 2, then Ph 3 P Me -60 C to 0 C 75%, 1 pot 16:1 Z/E Me DIBAL, C C PPh 3, C 4, C 3 C 0 C to r.t. 91% 97% Austin, D. J., et. al., rg. Lett. 2003, 5,
7 + The Pauson-Khand Approach DBU, DMF 94% TM TM , C % 2 BC 2, ac 3 1,4-dioxane 79% BC A TM TM B 1. A, then a then B, DMF, 50 C 2. K 2 C 3, Me 0 C to r.t. 83% BC 1. Co 2 (C) 8 C Et 3 0 C to r.t. dr = 4:1 BC 69%, 2 steps Austin, D. J., et. al., rg. Lett. 2003, 5, The Pauson-Khand Approach ydrogenation 2 2 BC a(g) mi 2, TF/Et BC BC 49% 2 BC Pd/C 57 psi 2 Et (95%) LiB 4, TF 0 C (80%) BC 0.1M mi 2 TF/ 2 (70%) or a(g), a 2 P 4 Et, 0 C (77%) BC Austin, D. J., et. al., rg. Lett. 2003, 5,
8 tudies on Absolute Configuration of a Pyrrolopyrazinone related to Palau'amine R CD pectral Features of two synthetic models: 10a 10 Positive Elipticity at 250nm, due to stereocenter 10a trong Band that sits at 285nm, due to stereocenter 10 R 10a 10 Positive Elipticity at 250nm, due to stereocenter 10a Weak shoulder that sits at 285nm, due to stereocenter 10 Whether R is Ac, R-MTPA, -MTPA or just, the CD spectrum is virtually unchanged! 2 2 Circular Dichroism tudies 10? 10a? (-)-Dibromophakellin CD Features egative Elipticity at 250nm, so the stereocenter at 10a is R. Weak houlder is observed at 285nm indicating that the stereocenter at 10 is. The authors are currently investigating the CD features of Palau'amine. Lindel, T., et. al., Chem. Eur. J. 2004, 10, Another Biosynthetic ypothesis Driven ynthetic Effort The ypothesis: = Dibromophakellins = Proposed (4 +2) 2-amino-1-(2-aminoimidazolyl) prop-1-ene (AAPE) --a known metabolite Romo(Texas A&M) rg. Lett. 2001, 3, Chloroperoxidase Mediated xidation and Rearrangement 8
9 Building the Diels-Alder Fragments 2 2 Ts 5 -teps TIP 2 ()-pyroglutamic acid 1. a DMF 41% 2. DIBAL- DCM -78 C 84 % 1. Mn 2 DCM 98% 2. (Et) 2 P()C 2 C 2 Et, a Et DIBAL- DCM -78 C 78 % Key Diels-Alder / Ring Contraction equence 2 2 TIP Ts Ph-, 2,6 Lut 95 C, 4 d TIP Ts 2 TIP Ts 64 % 15 % TIP Ts 1. TB 2. DMD, Mg 4 DCM, -45 C then DM, 99 % TIP Ts TBC, DCM, 75% TIP Ts TB 9
10 TIP Ts Cbz TB Palau'amine Retrosynthetic ummary TIP Ts Romo 2 2 Cbz TB verman 2 C 2 Me Austin Cbz Me R R Me
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