. Author manuscript; available in PMC: 2013 Mar 7.

Published in final edited form as: J Med Chem. 2012 Feb 21;55(5):2324–2341. doi: 10.1021/jm201556r

Table 1.

Diels-Alder Reaction of Thiophene 1 and Dienophiles 8.

Entry	Thiophene	Dienophile	Conv.^a(%)	Product Yield^b
1	1a	8a	55	10a (36%)
2		8b	58	10b (36%)
3		8k	60	10c (32%)
4		8l	59	10d (36%)
5		8m	59	10e (21%)
6	1b	8a	52	11a (41%)
7		8b	60	11b (26%)
8		8c	59	11c (40%)
9		8d	57	11d (31%)
10		8e	57	11e (35%)
11	1b	8f	54	11f (28%)
12		8g	57	11g (28%)
13		8h	54	11h (32%)
14		8i	56	11i (28%)
15		8j	55	11j (33%)
16		8k	64	11k (24%)
17		8l	60	11l (34%)
18	1c	8a	56	12a (50%)
19		8b	59	12b (27%)
20	1c	8c	54	12c (32%)
21		8d	53	12d (34%)
22		8e	58	12e (32%)
23		8j	56	12f (37%)
24		8k	59	12g (15%)
25		8l	58	12h (39%)
26		8m	59	12i (18%)
27	1d	8k	59	13 (55%)
28	1e	8k	54	14 (49%)
29	1f	8k	59	15 (35%)

The conversion was calculated accounting for the recovered thiophene.

Isolated yield by column chromatography purification based on the thiophene consumed.