[(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
hydrogenchloride in tetrahydrofuran; water; acetic acid
9 h; Ambient temperature;
参考文献
Kuo, C. H.; Patchett, A. A.; Wendler, N. L.
Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 1991 - 1998
→
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: 75.4 percent / toluene / 0.5 h / Heating
2: 63 percent / triethyl phosphite / 140 h / Heating
3: 4.0 mg / 2.5 N aqueous HCl / acetic acid; H2O; tetrahydrofuran / 9 h / Ambient temperature
View Scheme
参考文献
Kuo, C. H.; Patchett, A. A.; Wendler, N. L.
Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 1991 - 1998
→
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: 63 percent / triethyl phosphite / 140 h / Heating
2: 4.0 mg / 2.5 N aqueous HCl / acetic acid; H2O; tetrahydrofuran / 9 h / Ambient temperature
View Scheme
参考文献
Kuo, C. H.; Patchett, A. A.; Wendler, N. L.
Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 1991 - 1998
→
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 deg C, 15 min 2.) -60 deg C, 15 min
2: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
3: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
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: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
2: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
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 / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
2: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
3: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
4: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
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: 80 percent / n-tetrabutylammonium iodide, NaH / tetrahydrofuran / 18 h / Ambient temperature
2: 85 percent / 48percent aq. HF / acetonitrile / 1.5 h / Ambient temperature
3: 1.) oxalyl chloride, DMSO 2.) triethylamine / 1.) CH2Cl2, -60 deg C, 15 min 2.) -60 deg C, 15 min
4: 78 percent / BF3.Et2O, bis(trimethylsilyl)peroxide / CH2Cl2 / 1.5 h / Ambient temperature; 2
5: 42 percent / boron trichloride / CH2Cl2; hexane / 4 h / -78 °C
View Scheme
参考文献
Hanessian; Roy; Petrini; Hodges; Di Fabio; Carganico
Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5766 - 5777
→
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: Me3SiCl, NaI / acetonitrile / 0.5 h
2: benzene / 5 h / 80 °C
3: BF3*Et2O / CH2Cl2 / 15 h
5: DCC, DMAP / CH2Cl2 / 72 h
6: 10percent HCl / tetrahydrofuran / 4 h / 50 °C
7: PCC-Al2O3 / CH2Cl2 / 8 h
8: 48percent HF / acetonitrile / 6 h / 50 °C
View Scheme
参考文献
Falck; Yang
Tetrahedron Letters, 1984 , vol. 25, # 33 p. 3563 - 3566
→
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
2: DCC, DMAP / CH2Cl2 / 72 h
3: 10percent HCl / tetrahydrofuran / 4 h / 50 °C
4: PCC-Al2O3 / CH2Cl2 / 8 h
5: 48percent HF / acetonitrile / 6 h / 50 °C
View Scheme
参考文献
Falck; Yang
Tetrahedron Letters, 1984 , vol. 25, # 33 p. 3563 - 3566
→
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.) tosylation reagent 2.) NaI / 2.) acetone
3: DCC, DMAP / CH2Cl2 / 72 h
4: 10percent HCl / tetrahydrofuran / 4 h / 50 °C
5: PCC-Al2O3 / CH2Cl2 / 8 h
6: 48percent HF / acetonitrile / 6 h / 50 °C
View Scheme
参考文献
Falck; Yang
Tetrahedron Letters, 1984 , vol. 25, # 33 p. 3563 - 3566
