Hennoxazole A. Philip Williams Group Meeting December 12, OMe. OMe 1 6 O H
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1 ennoxazole A Philip Williams Group eting December 12, 2007
2 Discovered Discovered by Paul cheuer at the University of awaii in Isolated 480mg ennoxazole A from 4.5kg from the sponge Polyfibrospongia species. Also obtained ennoxazoles B D, though smaller amounts. Initial bio activity assays displayed that ennoxazole A is activeagainst against herpes simplex virus type 1 (IC μg/ml) and has peripheral analgesic activity similar to indomethacin when tested in mice. The absolute stereochemistry was not fully determined. cheuer, P. J., et. al, J. Am. Chem. oc., , 3173
3 tructure and Design (+) ennoxazole A Cl Cl Muscoride A Diazonamideid A xazole xazoline xazolidine 2-xazolidinone
4 etro? (+) ennoxaxole A Total yntheses: Wipf, Williams, hioiri, and mith.
5 etro 1996 Wipf Br I Wipf was the first to synthesize ennoxazole A. Designed his endgame to couple the bis oxazole moiety last the big challenge. emember, he didn t know the stereochemistry at C8 and C22! Wipf, P., et. al, Chimia, (4), 157.
6 etro 1999 Williams, D Piv C X X = Ph Piv nbu 3 + TBDP Concern over the stability of the skipped triene caused Williams to build that in to the molecule last. Williams, D., et. al, J. Am. Chem. oc., , 4924.
7 etro 2007 mith Br 11 mith intended to apply some of the oxazole alkylation work his lab had been working on. mith, T.E., et. al., J. rg. Chem AAP
8 Wipf s ynthesis Western alf Br 6M a BnEt 3 Cl Br BuLi, -78 to r.t. 1. MCPBA 2. Et 2, 1. harpless Epox. 2. ed-al, TF, Tol. 1. TBDM-Cl, Imid., C 2 Cl 2 2. Li, 3, t-amyl alcohol TBDM 1. 3 TBDM Ts, TF 2. 2,Pd() 2 TBDM ab 4,CeCl 3 TBDM 1. TIP-Cl 2. PPTs,, () 3 C 3. Li, dioxane/et/ 2 TIP 1. M, TPAP 2. (Et 2 ) 2 P()C 2 C 2 Et TIP 1. DIBAL-, TF 2. harpless Epox. TIP Absolute configuration of C8 stereocenter was chosen arbitrarily. Et Installing the desired anomer of the mixed acetal was challenging due to the potential elimination of the beta silyl ether. Wipf, P., et. al, Chimia, (4), 157.
9 Wipf s ynthesis Western alf TIP TIP BnC, TEA, C 2 Cl 2 Bn a, TF TIP 6.7:1 Bn 1. a, I 2. Li, dioxane/et/ 2 3. Pd() 2,Et, 2 TIP 2 Urethane cyclization proceded in a 6.7:1 ratio of isomers. 22 steps, 5% yield. Wipf, P., et. al, Chimia, (4), 157.
10 Wipf s ynthesis Eastern alf (Ph)(Bu 3 n)culi nbu 3 catecholborane Bu ()-oxazaborolidine 3 n 2,6-lutidine C Cl Bu 3 n TMB 2 CuLi Bu 3 n 2 TBDM , g 4 2. TBDM-Cl, Imid. 3. C() 3, + 4. Li, 2, TF TBDM TBDM 1. er-, IBCF 2. Burgess eagent Et 3 CuBr 2,MTA DBU, C 2 Cl 2 1. TBAF 2. B, Ph 3 P Br EWG was critical for first oxazole formation. thyl stereocenter at C22 was also arbitrarilychosen Wipf, P., et. al, Chimia, (4), 157.
11 Wipf s ynthesis coupling Pd 0 tille Coupling Bu 3 n Br I 2 1. t-buli I 2. ZnCl 2 3. Pd 2 (dba) 3 CCl 3 (5 mol%) Ph 3 As (20 mol%) 4. Li, 2 Br Bu 3 n tille coupling failed presumably due to the severe A 1 3 strain of the stannane.
12 Wipf s ynthesis Endgame TIP TIP P-Br PF DMP 2. BrCl 2 C-CCl 2 Br, Ph 3 P 3. DBU, C 3 C 4. TBAF (+) ennoxazole A 28 steps (longest sequence). pectroscopic investigation determined the natural stereoisomer of the natural product. Matches up with van t off s principle p of optical superposition. p
13 mith s ynthesis Western alf 2 -Cl Et -Cl 1. TEA 2. CuBr 2,DBU MTA 3. a, 2 1. Cl 2,reflux 2. er--cl, TEA 1. Deoxo-Fluor 2. DBU, BrCCl 3 3. DIBAL- TM, TMTf n-buli, TBTf =TB F 3 Deoxo-Fluor mith, T.E., et. al., J. rg. Chem AAP
14 mith s ynthesis Western alf TE 1. soft enolization 2. dimethyl acetal BF 3 -Et 2 TE 1. DIBAL- 2. ipr n(tf) 2, -Et-piperidine then aldehyde ipr magnesiumm acetoacetate imid., DMF then 2M Cl ab 4,CeCl 3 2. TB-Cl, imid, DMAP 3. C() 3,,PPT TB TB Many of the current directed acetate aldol auxiliaries were tested. mith, T.E., et. al., J. rg. Chem AAP
15 mith s ynthesis Eastern alf K, Bu 3 nc 2 I then n-buli 1. DMP 2. a, (Et) 2 P()CC 2 Et 3. DIBAL- 4. MsCl, TEA - then LiBr Br mith s design of a [2,3] Wittig till rearrangement allowed him to access this fragment in 6 steps fewer than Williams synthesis. mith, T.E., et. al., J. rg. Chem AAP
16 mith s ynthesis Endgame 1. LiEt 2,then TB TB Br 2. TBAF (-) ennoxazole A 14 steps from commercially available materials. (really 17 steps ) Employed a one pot acylation/decarboxylation/cyclodehydration and determined the alkylation selectivities for bis oxazoles. mith, T.E., et. al., J. rg. Chem AAP
17 eferences cheuer, P. J., et. al, J. Am. Chem. oc., , Wipf, P., et. al, Chimia, (4), 157. Wipf, P., Miller, C.P., J. rg. Chem., , mith, T.E., et. al., J. rg. Chem AAP. mith, T.E., et. al., rg. Lett., (14), mith, TE T.E., Balskus, EP E.P., eterocycles, (7), mith, T.E., et. al., rg. Lett., (6), hioiri, T., et. al., rg. Lett., (26), hioiri, T., et. al., ynlett, , 109. hioiri, T., et. al., eterocycles, (8), 73. Leahy, J. W., et. al., ynlett, , 623. Williams, D.., et. al., Tett. Lett., (3), 331. Williams, D., et. al, J. Am. Chem. oc., , 4924.
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