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Efficient Synthesis of the N‐(buta‐2,3‐dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids

“…60-75 8C) were used after distillation. 1652,1606,1500,1438,1384,1330,1297,1257,1236,1166,1128,1097,1074,1056,991,910,806,754,696 -2-[(1R,4aR,4bS,7S,10aR)-1,4a,7-trimethyl-7-vinyl-1,2, 3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthren-1-yl 40 (m, 4H,2H-11, 12), 1.42-1.49 (m, 2H,2H-12), 1.51-1.78 (m, 12 H, 2H-11, 2, 3, 2, 6, 9), 1.80-1.84 (m, 4H,2H-14, 5), 1.86-2.01 (m, 8H,2H-14, 6, 3, 1), 3.52 (dd,J = 14.0,7.2 Hz,1H,3.55 (dd,J = 14.0,8.2 Hz,1H,4.85 (dd,J = 10.9,1.6 Hz,1H,4.87 (dd,J = 10.9,1.6 Hz,1H,4.91 (dd,J = 17.7,1.6 Hz,1H,4.92 (dd,J = 17.7,1.6 Hz,1H,4H,5'), 5.30 (br s, 1H, =CH 2 ), 5.37 (br s, 2H, =CH 2 ), 5.37 (s, 1H, =CH 2 ), 2H,[2][3][4][5][6][7][8]…”

“…25, 60.32 (2 C-4'), 79.50, 79.61 (2 C-5'), 109.08 (2 C-16), 111.79, 112.11( 2C-7'), 120.91, 121.06 (2 C-7), 126.36, 126.36 (4 C-2'',6''), 127.84 (2 C-4''), 128.32 (4 C-3'',5''), 135.43 (2 C-8), 137.81, 137.91 (2 C-6'), 147.18 (2 C-1''), 150.16 (2 C-15), 173.97, 174.12 ppm (2 C-2');IR: ñ = 2927IR: ñ = , 2869IR: ñ = , 2850IR: ñ = , 1650IR: ñ = , 1500IR: ñ = , 1384IR: ñ = , 1234IR: ñ = , 1139IR: ñ = , 1105IR: ñ = , 1031 4aR,4bS,7S,10aR) -1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10, (m, 10 H, 2H-11, 6, 2, 12, 2), 1. 68-1.78 (m, 4H,2 H-6, 9),1.79-2.03 (m, 10 H, 2H-1, 14, 14, 3, 5) 2869, 2846, 1648, 1598, 1500, 1461, 1436, 1384, 1292, 1247, 1240, 1182, 1139, 1126, 1095, 1047, 1027, 985, 912, 870, 754 cm (1R,4aR,4bS,7S,10aR) 4a,2,3,4,4a,4b,5,6,7,8,10, (m, 2H,2H-11), 1.32 (s, 3H,C 19 H 3 ), 1.34 (s, 3H,C 19 H 3 ), 1.31-1.39 (m, 2H,2H-12), 1.44-1.49 (m, 2H,2H-12), 1.52-1.68 (m, 10 H, 2H-11, 2, 3, 2, 6), 1.70-1.78 (m, 4H,2H-6, 9), 1.82-2.01 (m, 10 H, 2H-1, 14, 14, 3, 5) 6 Hz,1H,4.91 (dd,J = 17.7,1.6 Hz,1H,4.92 (dd,J = 17.7,1.6 Hz,1H,4H,5'), 5.32 (s, 2H, =CH 2 ), 5.34 (s, 2H, =CH 2 ), 5.36 (s, 1H, =CH 2 ), 5.76 (dd,…”

“…2 Hz,1H,4.03 (dd,J = 14.0,10.5 Hz,1H,4.85 (dd,J = 10.9,1.6 Hz,2H,[2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]4.91 (dd,J = 17.7,1.6 Hz,1H,4.92 (dd,J = 17.7,1.6 Hz,1H,, 5.21 (s, 1H, =CH 2 ), 5.29 (s, 1H, =CH 2 ), 5.30 (s,2H,=CH 2 ),4H,5'),5.77 (dd,J = 17.7,10.7 Hz,1H,5.81 (dd,J = 17.7,10.7 Hz,1H,6.83 (d,J = 8.6 Hz,2H,5 ''),6.85 (d,J = 8.8 Hz,2H,5 ''),6.83 (d,J = 8.6 Hz,2H,6 ''),6.85 ppm (d,…”

“…3-methylene-2-{[(1R,4aR,4bS,7S,10aR)-1,4a,7-trimethyl- 7-vinyl-1,2,3,4,4a,4b,5,6,7,8, 10,10a-dodecahydrophenanthrene-1-carboxamido]methyl}indoline-1-carboxylate (7): R f = 0.12 (CHCl 3 /EtOH, 10:1); 1 HNMR (500 MHz 5.76 (dd,J 17.6,10.7 Hz,1H,5.78 (dd,J 17.6,10.7 Hz,1H,4H,[2][3][4][5]6 '),7.23 (m,2H,[2][3][4]2H,[2][3][4][5][6][7]); 13 CNMR (126 MHz, CDCl 3 ): d = 14.00 (2 C-20), 15.11( 2C-11), 17.95 (2 C-2), 19.70 (2 C-19), 21.28 (2 C-17), 24.57 (C-6), 28.25 (6 C-2 (CH 3 ) 3 ), 34.90 (2 C-10), 35.95 (2 C-12), 36.64 (2 C-3), 37.08 (2 C-1), 38.54 (2 C-13), 41.72 (2 C-4), 45.23 (2 C-5), 46.84 (2 C-14), 46.05 (2 C-(CH 2 )), 51.70 (2 C-9), 60.18 (2 C(CH 3 Reaction of Terpenoid N-(2,3-Butadienyl)carboxamide 3w ith 2-Iodophenol (10) ( Table 2) Entry 1: Compound 10 (380 mg, 1.71 mmol), Cs 2 CO 3 (920 mg, 2.81 mmol), and Pd(PPh 3 ) 4 (80 mg, 0.07 mmol) were added to a stirred solution of 3 (500 mg, 1.41 mmol) in MeCN (2 mL) at RT under an argon atmosphere. The mixture was heated at 80 8Cf or 3h,c ooled, diluted with ethyl acetate (20 mL), washed with water (3 5mL), dried with K 2 CO 3 ,f iltered, and concentrated under reduced pressure.…”

“…For example,i sopimaric acid (1)i sareadily available and versatile tricyclic diterpenoid that is well represented in the resin of conifers of the genera Pinus, Larix,a nd Picea. [3,4] The attraction of compound 1 as ab iorenewable compound and its interesting biological and pharmaceutical properties, whichi nclude anti-bacterial, [5][6][7] antiviral, [8] anda nti-inflammatory [9] activities, has stimulated the development of av ariety of chemistries for functionality,i ncluding oxidative [10][11][12] and isomeric [13] transformations, in addition to several modificationso ft he carboxyl group. [14,15] The number of examples in the literature detailing the functionalization of isopimaric acid is limited,a nd they do not result in the generation of evolvable libraries of compounds for structure-activity relationship studies.…”