BURIED TREASURES: CASCADES WE AVE'T SEE Me Me Me 2 3 C C 3 3 C C 3 C 2 Me R. Robinson, J. Chem. Soc., 1917, 762
Cascades Articulated Main Entry: 1cas cade Pronunciation: (")kas-'kad Function: noun Etymology: French, from Italian cascata, from cascare to fall, from (assumed) Vulgar Latin casicare, from Latin casus fall, Date: 1641 1: a steep usually small fall of water; especially :one of a series 2a : something arranged or occurring in a series or in a succession of stages so that each stage derives from or acts upon the product of the preceding <blood clotting involves a biochemical cascade > b: a fall of material (as lace) that hangs in a zigzag line 3: something falling or rushing forth in quantity <a cascade of sound> <a cascade of events> 4: ne-pot, sequential reactions involving more than one intermediate, preferrably 1) leading to an increase in molecular complexity and 2) without changing reaction conditions see: Chem. Commun., 2003, 551
Cascades Articulated Main Entry: 1cas cade Pronunciation: (")kas-'kad Function: noun Etymology: French, from Italian cascata, from cascare to fall, from (assumed) Vulgar Latin casicare, from Latin casus fall, Date: 1641 1: a steep usually small fall of water; especially :one of a series 2a : something arranged or occurring in a series or in a succession of stages so that each stage derives from or acts upon the product of the preceding <blood clotting involves a biochemical cascade > b: a fall of material (as lace) that hangs in a zigzag line 3: something falling or rushing forth in quantity <a cascade of sound> <a cascade of events> 4: ne-pot, sequential reactions involving more than one intermediate, preferrably 1) leading to an increase in molecular complexity and 2) without changing reaction conditions see: Chem. Commun., 2003, 551
Some Inspiration C 2 Me icolaou, K. C., J. Amer. Chem. Soc., 1982, 5555 1) 2, Pd/BaS 4 quinoline 2) toluene, 100 C 3 intermediates C 2 Me Me Me Me, TFA, 1,2-dichloroethane; Me Me Me K 2 C 3, 2, Me Johnson, W. S., J. Amer. Chem. Soc., 1971, 4330 2 intermediates Me 3 C P P R C 3 P Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 Se mcpba, C 2 Cl 2 ; 40 C, CCl 3 4 intermediates P 1 3 C 3 C R P 1 P 2 C 3 C 3
Some Inspiration C 2 Me icolaou, K. C., J. Amer. Chem. Soc., 1982, 5555 1) 2, Pd/BaS 4 quinoline 2) toluene, 100 C 3 intermediates C 2 Me Me Me Me, TFA, 1,2-dichloroethane; Me Me Me K 2 C 3, 2, Me Johnson, W. S., J. Amer. Chem. Soc., 1971, 4330 2 intermediates Me 3 C P P R C 3 P Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 Se mcpba, C 2 Cl 2 ; 40 C, CCl 3 4 intermediates P 1 3 C 3 C R P 1 P 2 C 3 C 3
Some Inspiration C 2 Me icolaou, K. C., J. Amer. Chem. Soc., 1982, 5555 1) 2, Pd/BaS 4 quinoline 2) toluene, 100 C 3 intermediates C 2 Me Me Me Me, TFA, 1,2-dichloroethane; Me Me Me K 2 C 3, 2, Me Johnson, W. S., J. Amer. Chem. Soc., 1971, 4330 2 intermediates Me 3 C P P R C 3 P Sorensen, E. J., J. Amer. Chem. Soc., 2002, 4552 Se mcpba, C 2 Cl 2 ; 40 C, CCl 3 4 intermediates P 1 3 C 3 C R P 1 P 2 C 3 C 3
Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
Dihydropyridone Synthesis Chem. arm. Bull., 1987, 4730 Et, hu Et Me 2 C -C Me 2 C Me 2 C Me 2 C
Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
Degredation to a Cyclohexadiene Angew. Chem. Int. Ed., 1975, 765. C 3 Li Et 2 C 3 Li
C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, 496 1. C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, 496 1. C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, 496 1. C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, 496 1. C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
C 2 I 2, Zn/Cu Starting Material? Angew. Chem. Intern. Ed., 1975, 496 1. C 2 I 2, Zn/Cu 2. C 3 3. MeLi, Et 2 C 3, KtBu MeLi Li Et 2
Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
Synthesis of a Tetrayne Tetrahedron Lett., 1976, 2663 Ac BuLi; CuCl BuLi Cu + Ac Li Cu + Ac Cu Symmetry Forbidden
Complex Polycycle J. Am. Chem. Soc., 2001, 12107 Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
Complex Polycycle J. Am. Chem. Soc., 2001, 12107 Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
Complex Polycycle J. Am. Chem. Soc., 2001, 12107 Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
Complex Polycycle J. Am. Chem. Soc., 2001, 12107 Bu 3 Sn SnBu 3 Pd(P 3 ) 4, D xidative Addition PdL n Migratory Insertion PdL n Transmetallation Bu 3 Sn SnBu 3 SnBu 3
Complex Polycycle Cont... J. Am. Chem. Soc., 2001, 12107 6 e- disrotatory - SnBu 3 SnBu 3 1 transfer -
Complex Polycycle Cont... J. Am. Chem. Soc., 2001, 12107 6 e- disrotatory - SnBu 3 SnBu 3 1 transfer -
A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
A [3.2.0] Bicycle J. rg. Chem., 1994, 8092 Me 2 C TBDPS Si I TMSI, (TMS) 2 TBDPS I TMS C 2 Me TMS 2 TBDPS I - TMS C 2 Me TBDPS I Me TMS + TBDPS I C 2 Me TMS
A ydrindane Unpublished P 3, D P 3 P() 3
A ydrindane Unpublished P 3, D P 3 P() 3
A ydrindane Unpublished P 3, D P 3 P() 3
Another (the same) ydrindane oye, T., Unpublished Bn Grubbs Bn Bn Bn Bn Bn Bn
Another (the same) ydrindane oye, T., Unpublished Bn Grubbs Bn Bn Bn Bn Bn Bn
Another (the same) ydrindane oye, T., Unpublished Bn Grubbs Bn Bn Bn Bn Bn Bn
Summary Et, hu Et Me 2 C TBDPS TMSI (TMS) 2 I TBDPS TMS C 2 Me C 3 Li MeLi, Et 2 Et 2 Ac BuLi; CuCl P 3, D Bu 3 Sn SnBu 3 Bn Grubbs Bn Pd(P 3 ) 4, D