Synthesis of the Phomoidrides (CP 225,917 & CP 263,114) Chem. Rev. 2003, 103, 2691.
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1 ynthesis of the Phomoidrides (P 225,917 & P 263,114) hem. Rev. 2003, 103, (+)-P hom oidr ide A ; 7 = (P- 225,917) (+)-P hom oidr ide ; 7 = R Li + Isolated from a fungus found on the twigs of a juniper tree in Texas (Pfizer, 1997) Found to inhibit Ras farnesyl transferase and squalene synthase - In studies as cholesterol lowering and anti-cancer drugs 1 5 Relative configuration determined by NMR analysis Absolute configuration determined by synthesis (Nicolaou, 2000) 4 total syntheses and >18 partial syntheses (- )-Phomoidr ide B ; 7 = (P- 263,114) (- )-Phomoidr ide D; 7 = R Key features are a [4.3.1] bicyclo system containing a bridgehead double bond; quat center (14); and maleic anhydride moiety All four compounds have been isolated from natural sources
2 Proposed Biosynthesis ulikowski; JA, 2000, 122, 420. succinic acid oa oxaloacetyl-oa Enz oa acetyl oa oa 15 Enz Enz 15 Enz Enz 15 Enz Enz head to head dimerization 15 Phomoidride B ydrolyze - 2 xidize 15 Enz Enz
3 Nicolaou s Total ynthesis Angew. hem. Int. Ed. 1999, 38, 1669; 1676 TB DP P MB M e 2 All 90% TBDP 15 PM B 1. TBAF 2.DM P 3. Li 4. Na, T E Tf 15 TE PM B 67% 1. KM D, PhNT f 2 2. Pd(A c) 2,, PPh 3, Me 3. PhI( 2 F 3 ) 2, M e 62% Me Me TE P MB 1. Ms l, Et 3 N 2. K 2 3, Me; 10% ox alic ac id M e M e 15 TE PM B N 1. DIBAL 2. V( )(acac) 2, tbu 3. Et 2 AlN Me Me 1 5 TE P MB 2 Me 56% 55%
4 Nicolaou cont. Me Me T E P MB 1. A c TB 1. PD M e 2 ( Me) 2, A 3. TB T f 4. DDQ 2. Ac 44% 1 5 TB 1. TE Tf 2. DM P 67% 15 TB 1. TFA, Ms 2. DM P 3. TB Tf 63% TE 15 TB 1. Nal 2 2. Ms l 3. 2 N 2 4. Ag 2 32% 15 TB
5 ompletion of Nicolaou s ynthesis TB 1. ED, 2. TFA 3. DM P 65% N p-chloroanil N Li 50% 1 5 N % (±) P hom oidride A (±) Phom oidride B
6 Nicolaou s Asymmetric ynthesis-determination of Absolute onfiguration Angew. hem. Int. Ed. 2000, 39, 1829 TB TB P MB 15 l 2 Al tb u tbu P MB 88% 1 5 T B TB T B TB PM B 5.7:1 1. T BAF 2. NaI 4 P MB 15 N (+)- Phom oidride B ompared with compound obtained from natural source: opposite rotation
7 Fukuyama s ynthesis- 1 st Asymmetric ynthesis of Natural Enantiomer JA 2000, 122, 7825 aldol addition N Et B n Me 2 2 M e cupr ate additi on Znl 2 Et X c 7-s teps Me 2 2 M e E t M e 2 2 M e 1. Li; Ba() 2 2. Ar ndt-eistert 54% 1. Jones % E t Me 2 2 tbu 1. m-p BA 2. TFAA, DIEA 3. Ac 51% 2 tb u (-)- Phom oidride B
8 Danishefsky s Total ynthesis: Insight into 7 onfiguration Angew. hem. Int. Ed. 1999, 38, 1485; 1999, 38, 3197 T B TB TB I racem ic TB aldol additi on 1. P d( Ac) 2 ( PPh 3 ) 2 2. DIBA L 3. TB Tf TB TB 1. e 2 2. TPA P, NM 3. I 2, pyr 56% 73% TB I TB 1. B(( 2 ) 6 B n) 3, P dl 2 (dppf) 2. F, pyr 3. Til 4, A lly ltm 47% T B TB 1. M sl 2. DBU TB TB 1. LA 2. wer n TB TB ( 2 ) 6 B n 57%-four steps ( 2 ) 6 B n ( 2 ) 6 Bn
9 Danishefsky cont. TB TB TB Tebbe olefination 2. Zn, trichloroacetyl chloride 3. Zn, N 4 l, Me 4. TBAF Bn( 2 ) 6 TB ( 2 ) 6 Bn 43% ( 2 ) 6 Bn Tebbe reagent: p2 Ti AlMe 2 l 1. PhPh, Na, K 2. DMP 72% TB 7 = R Ph ( 2 ) 6 Bn , Me 2. s 4, NM 49% TB Ph ( 2 ) 6 Bn
10 ompletion of 7-epi Phomoidride B TB Ph ( 2 ) 6 Bn Bn( 2 ) 6 TB Ph 1. NaM e 2. wern 3. B rmg 4. DMP 25% Bn( 2 ) 6 2 Me TB 1. DDQ 2. DM P 3. 1,1-diiodoethane, rl 2 34% 7 1. Li 1. hv, Rose bengal TB Ms 81% 15 2 M e 2. TPA P, NM 50% Me ( ±) -Phomoidride D (7 = R) =
11 The 7 onfiguration 15 (decomp.) 15 Phomoidride D (7 = R) more stable + Phomoidride B (7 = ): originally isolated species 7 step sequence TB Ph P b( Ac) 4 TB Ph Li TB P h ( 2 ) 6 Bn ( 2 ) 6 Bn ( 2 ) 6 B n 10:1 favori ng undesir ed
12 hair s Total ynthesis of ent-phomoidride B JA, 2000, 122, tille cuprate addition ( ±) 2 Me P MB (+)- Me B, catechol borane 31%, 90%ee 2 M e PM B 5 B rmg M M (from (R)-glyceraldehyde 53% M e MM Me M M BrM g PM B anion acceler ated oxy- ope B rmg P MB 1 5 trans annular Dieck mann cy cli zation M M PM B KMD, N 2 Me 2. Bl 3 3. DM P 4. Nal 2 Me 2 MM 1 5 Me 2 1. M Ml 2. KM D, N 2 M e Me MM M e
13 ompletion of hair s ynthesis Me 2 Me MM Me TM Tf M e 2 1. M sl, Et 3 N, then 2 N 2 (M e) 3 2. hv, tbu 40% ov er 7 12% steps 15 Me 2 1. KNiP r 2, Tf 2 2. Pd(A c) 2,, P (M e) % tbu (+) phom oidride B
14 Leighton s Approach J, 2003, 68, 1693 Me 2 Me M e 2 Me l l 200 o + 74% Me 2 l l M e l M e l l l 2 Me T E Tf TB DP 1. Li 5.7:1 2. M ei, Na 3 3. Zn(B 4 ) 2 45% 15 TE Tf TBDP P d( PP h 3 ) 4, DIEA 78% TE TBDP [3,3] 1 5 TE TBDP TE TBDP
15 Wood's Approach: rg. Lett. 2001, 3, 2435 Me 2 Me 2 Me 2 2 M e 2 M e 2 M e M e 2 M e 2 P b( Ac) 4 90% mi 2, T F MP A 60% M e 2 M e 2 M e 2 2 M e M e LiTMP N I 40% 1. B F 3 Et 2. Raney Ni 3. K, 2, M ei M e 2 M e 2 Me 2 Et 1. Br B r N,N-dimethy lanaline 2. B u 3 n, AIB N 7:3, 60% 2 Me 5-exo-5-exo trig Me Me Et Et 6-endo-4-exo trig
16 Tin-Free Deoxygenation JA, AAP Me 2 Me 2 Me BMe 3, 2 Me 2 Me 2 Proposed Mechanism Initiation: BMe Me Propagation Me 2 B- + R- Me R Me Me R' R Me Me 3 B R
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