[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯合成路线 （共 63 条）
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
toluene-4-sulfonic acid in benzene
0.666667 h; Ambient temperature;
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
2: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
3: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
2: 96 percent / DMAP / pyridine / 3.33 h / 50 °C
3: 96 percent / KOH / methanol / 8.5 h / Ambient temperature
4: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
5: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
6: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
7: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
8: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 99 percent / quinoline, hydrogen / Pd/BaSO4 / 50 h
2: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating
3: 95 percent / m-PCBA / CH2Cl2 / 1 h / 0 °C
4: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature
5: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating
6: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature
7: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C
8: 85 percent / HCl / methanol / 15 h / 0 °C
9: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min
10: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
11: 96 percent / DMAP / pyridine / 3.33 h / 50 °C
12: 96 percent / KOH / methanol / 8.5 h / Ambient temperature
13: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
14: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
15: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
16: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
17: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating
2: 95 percent / m-PCBA / CH2Cl2 / 1 h / 0 °C
3: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature
4: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating
5: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature
6: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C
7: 85 percent / HCl / methanol / 15 h / 0 °C
8: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min
9: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
10: 96 percent / DMAP / pyridine / 3.33 h / 50 °C
11: 96 percent / KOH / methanol / 8.5 h / Ambient temperature
12: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
13: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
14: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
15: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
16: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 94 percent / methanol / 18 h / Ambient temperature
2: 86 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / 2 °C
3: 99 percent / quinoline, hydrogen / Pd/BaSO4 / 50 h
4: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating
5: 95 percent / m-PCBA / CH2Cl2 / 1 h / 0 °C
6: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature
7: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating
8: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature
9: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C
10: 85 percent / HCl / methanol / 15 h / 0 °C
11: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min
12: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
13: 96 percent / DMAP / pyridine / 3.33 h / 50 °C
14: 96 percent / KOH / methanol / 8.5 h / Ambient temperature
15: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
16: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
17: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
18: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
19: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature
2: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating
3: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature
4: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C
5: 85 percent / HCl / methanol / 15 h / 0 °C
6: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min
7: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
8: 96 percent / DMAP / pyridine / 3.33 h / 50 °C
9: 96 percent / KOH / methanol / 8.5 h / Ambient temperature
10: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
11: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
12: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
13: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
14: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 95 percent / m-PCBA / CH2Cl2 / 1 h / 0 °C
2: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature
3: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating
4: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature
5: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C
6: 85 percent / HCl / methanol / 15 h / 0 °C
7: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min
8: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
9: 96 percent / DMAP / pyridine / 3.33 h / 50 °C
10: 96 percent / KOH / methanol / 8.5 h / Ambient temperature
11: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
12: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
13: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
14: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
15: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
2: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
3: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
4: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
5: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
→
77517-29-4[(1S,3S,4aR,7S,8S,8aR)-8-[2-[(2R,4R)-4-羟基-6-氧代四氢吡喃-2-基]乙基]-3,7-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-基] (2S)-2-甲基丁酸酯
反应条件
1: 85 percent / ozone, dimethyl sulfide / CH2Cl2 / 18 h / 40 °C / Heating
2: 91 percent / DBU / CH2Cl2 / 1 h / Ambient temperature
3: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C
4: 85 percent / HCl / methanol / 15 h / 0 °C
5: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min
6: DMAP, 1,3-dicyclohexylcarbodiimide / CH2Cl2 / 0 °C
7: 96 percent / DMAP / pyridine / 3.33 h / 50 °C
8: 96 percent / KOH / methanol / 8.5 h / Ambient temperature
9: 1.) oxalyl chloride, DMSO; 2.) triethylamine / 1.) CH2Cl2, -60- -50 deg C, 15 min; 2.) -60- -50 deg C, 5 min
10: 45 percent / LiCl, DBU / dimethylsulfoxide / 39 h / Ambient temperature
11: 1.) triethylsilane; 2.) 48 percent aq. HF / 1.) (PPh3)3RhCl / 1.) benzene, 70 deg C, 40 min; 2.) CH3CN, rt. 50 min
12: 39 percent / NaBH4 / methanol / 0.75 h / Ambient temperature
13: 85 percent / p-Ts-OH*H2O / benzene / 0.67 h / Ambient temperature
View Scheme
参考文献
Hecker, Scott J.; Heathcock, Clayton H.
Journal of the American Chemical Society, 1986 , vol. 108, # 15 p. 4586 - 4594
