ISOCHRYSOHERMIDIN. MeO 2 C. MeO. MeO. MeO 2 C OH. Me 1
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1 ISCRYSERMIDI 2 C 2 C 1
2 ormal demand Diels-Alder (M diene - LUM dienophile ) eutral Diels-Alder Inverse demand Diels-Alder (LUM diene - M dienophile ) EDG EWG EWG EDG LUM LUM LUM M E 1 E 2 E 3 M M E Scheme 1. Classification of Diels-Alder s and their corresponding energy diagrams. EDG = electron donating group, EWG = electron withdrawing group.
3 Br 2 Bn A 2 B 2 S 2 C 3 C 6: streptonigrone 3 1 D benzene, 30 min, 25 C Inverseelectrondemand Br Br Bn Bn t-buk, TF, -30 C; then DDQ 4 5 S 2 C 3 (65% from 2) Scheme 2. Boger's total synthesis of streptonigrone (6) featuring an inverse electron demand Diels-Alder of a -sulfonyl-1-aza-1,3-butadiene (2).
4 7 C + -[ 2 ] (87%) 13 C 2 C 2 8 TBS Retro-Diels Alder TBS dioxane, 60 C, 21.5 h Inverseelectron-demand TIPB, 230 C, h Azadiene TBS C 2 C -[ 2 ] C 2 Retro 2 C Diels 2 C C Alder 9 10 TIPB = 1,3,5-triisopropylbenzene 12 C steps Aromatization 2 C 11 -[] (70%) 2 C 2 14 C 15: (+)-CC-1065 Scheme 3. Use of 1,2,4,5-tetrazine 8 in an inverse electron demand Diels-Alder followed by an intramolecular 1,2-diazine/alkyne cycloaddition in Boger's total synthesis of (+)-CC-1065 (15).
5 C 2 Et Cl 2 C 2 Et C 2 Et Et 2 C C 2 Et C 2 Et DMF, 90 C, 24 h -[ 3 ] Inverse electron demand 2 C 2 Et C 2 Et 16 Diels-Alder C 2 Et C 2 C 2 23: pyrimidoblamic acid steps 2 C 2 Et C 2 Et 22 -[Et 2 CC] (85%) Retro Diels-Alder Tautomerization 2 C 2 Et C 2 Et 21 C 2 Et Scheme 4. A 1,3,5-triazine/amidine Diels-Alder as part of Boger's synthesis of pyridoblamic acid (23), a key intermediate for the total synthesis of bleomycin A 2.
6 2 C 2 C 1: (+)-isochrysohermidin 2 C 5 3 3' 2 26 C 2 5' 2' C 2 C 2 Double reductive ring contraction Tandem endoperoxide fragmentation -thylation Selective ester hydrolysis 2 C 2 C 2 C 24 Double 1 2 C 2 2 C 25 C 2 C 2 2 C 2 C 27 C 2 C 2 Double azadiene + C 2 C 2 28: dienophile 8: diene Scheme 5. Retrosynthetic analysis of isochrysohermidin (1).
7 C 2 + C 2 28: dienophile 8: diene C 2 C 2 2 C C [ Retro-Diels 2 ] Alder CCl 3, 60 C, 5 days Inverseelectron-demand 8 Inverseelectron-demand R R 29: R = C 2 Retro-Diels Alder -[ 2] 2 C 30 C 2 2 C 2 C 32 C 2 C 2 -[] (65%) Aromatization 2 C 2 C 27 C 2 C 2 Scheme 6. Initial double azadiene Diels-Alder /retro Diels-Alder process leading to key biaryl intermediate 27.
8 2 C 2 C 2 C 2 C C 2 C 2 Zn, Ac 22 C, 24 h 2 C C 2 C 2 Reductive cleavage 2 C 2 C 2 C Enamine-Imine condensation -[ 3 ] (68%) C 2 C 2 C 2 Li 5' 2' a, I, DMF C 2 (100%) C 2 (98%) C 2 2 C 37 C 2 2 C C 2 2 C 26 C 2 TFAA C 2 C 2 C 2 2 C C C 2 (83% from 37) 2 C C 2 C Scheme 7. Synthesis of the advanced key intermediate 25.
9 C 2 C 2 2 C C , ( 2, rose bengal, hν) collidine/ 2 /i-pr (2:6:1) 22 C, 1 h Double Diels-Alder 2 C 2 C 1: (+)-isochrysohermidin 2 C 2 C 2 C 24 -[C 2 ] (~70%; 40% d,l-1, 30% meso-1) Endoperoxide fragmentation Scheme 8. Completion of the synthesis of isochrysohermidin (1).
10 C 2 2 C 40 2 C 2 C 1: (+)-isochrysohermidin 1 2, (PPh 3 3 ) C 2 Cl 2 22 C, 1 h Double Diels-Alder (42%) (1:1 ratio of d,l- and meso-1) 2 C 2 C 41 omolytic cleavage 2 C 2 C 42 X Scheme 9. Wasserman's alternative method of synthesizing isochrysohermidin (1) from the bis-pyrrole 40 using singlet oxygen.
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