The Diels-Alder Reaction

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		Ph		O				Ph H O
			+	O	PhMe, Rfx			O
					3 h, 80%
				O				H O
								1
	OSPDBT					OSPDBT			COOH
		t -Bu
		O O				O			OH
	+		PhMe, 120 C		O
		O					t-Bu
					O			O	O
O	O				O	O		O
						H			H
						H			H
Me3Si	OMOM						OMOM		OH
					Me3Si
						2			3

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Domino Knoevenagel hetero -Diels −Alder reactions [7]
			t-Bu		O
							O	t -Bu
O						t -Bu
	+ O		N	EDDA, MeCN			H
CHO		N		Rfx, 16 h, 94%			H	N
					O	N
		Ph						N
						N	O
						Ph		Ph
Cascade Diels−Alder acylation reactions [8]
OSMDBT						OSMDBT	O
N		O		THF, 50%	H N Cl		H N
	+
			Cl 2 h, −78 C, 24 h, 0 C			H O		H O
Domino Diels−Alder reactions [9]
Ph				O	Ph		O Ph
O +				100 C			Ph
				Ph
Ph

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Open chain	Outer ring	Inner-outer ring	Across ring	Inner ring

		O	O		O
OSiMe3
					N
	OMe		O		O
					O
		O
	O			O	O
			O
				O	O
		O

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reactive dienes

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				unreactive dienes
O	R1		O		R1	R2
	R2		AlCl3
+
			PhMe
						R3
	R3			H
R1, R2, R3 = H, Me
O				O
	OEt					CO2Et
CO2Et		90	C, 24 h
+			95%
						OEt
					H
Ph						O
Ar		Ar1			Ar	Ph
			60 C
O	+
			PhMe
Ar
				Ar		Ph Ar1
Ph

Ar = C6H4Y (Y = H, p-OMe, p-NMe2)

Ar1 = C6H4Y (Y = H, p-OMe, p-NMe2, p-Cl, p-NO2, m-NO2)

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		Acyclic				Cyclic
					O	O	O
CHO			COMe	CN
						O	N
(NC)2 (CN)2		MeO2CCH		CHCO2Me	O	O	O
						O
					O
H2C	C CHMe		HC	CO2Me		N
						N Ph
						N
Me2C	S	Ph	N O	ArN NCN		O
							O
O O		S	S	OEt		O	O

	O	O	H	O
+	O	O		O ! "
	O	O	H	O

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		H	H
	CF3SO3H, DCM		+
	−23 C, 1 h
		H	H
4		5	6
H		−H	−H
	H	H	H
			+
	H	H	H
7		8	9

" &! "

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O		Ph
Ph
H	Pd2+, CHCl3, 50 C, 20 h, 67%	O

			Ph
O Pd2+
Ph			O
H			Pd2+
			10
O	TMSOTf	O
			OMe
O	MeOSMT,
		O	11 h, 89%
O	DCM, −45 C		CO2CH2COCH3
11		11a

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O	O Li	CO2CH3	H	CO2CH3
LDA				H
−23 C, 1 h		−23 C, 2 h, 90%
			OLi
			O	Li
EtO2C	LDA			O
	−20 C, 2 h, 45%			OEt
	O

H CO2CH3

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O

EtO2C

O ! "

H

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			68 h, 25 C	O
			CHCl3, 14%
		O		NMe
	+	NMe		O	! "
				HO
O	OH	O
			15 min, 25 C
			DMF, 100%

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I		H
AIBN
n-Bu3SnH		H	! "
80 C, 8 h, 22%	O	H H
O	O	O
12	13	14

	Br		TTMSS		H		Br
		O	AIBN, PhMe		O		O
					O	+ R	O
	R O		85 C, 16−26%	R

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R = H, Me, Cy		O
	R	O