501369-39-7合成路线

501369-39-7

130595-24-3Phomactin A

参考文献

Mohr, Peter J.; Halcomb, Randall L.
Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1712 - 1713

501369-25-1

501369-39-7

参考文献

Mohr, Peter J.; Halcomb, Randall L. Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1712 - 1713

234078-11-6

501369-39-7

反应条件

Multi-step reaction with 18 steps 1.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C 1.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C 2.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C 3.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C 3.2: diethyl ether; petroleum ether / 1 h / -78 °C 4.1: 378 mg / triethylamine; methanesulfonyl chloride / CH2Cl2 / 4 h / 20 °C 5.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C 5.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C 5.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C 6.1: 91 percent / PCC / CH2Cl2 / 48 h / 20 °C 7.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 8.1: 173 mg / mCPBA / CH2Cl2 / 1 h / 0 °C 9.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 10.1: magnesium bromide diethyl etherate / CH2Cl2 / 12 h / -78 °C 11.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 12.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C 12.2: 77 percent / camphorsulfonic acid / CH2Cl2 / 18 h / 20 °C 13.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 14.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C 14.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C 15.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C 16.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C 16.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C 17.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 18.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

参考文献

Mohr, Peter J.; Halcomb, Randall L. Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1712 - 1713

501369-28-4

501369-39-7

反应条件

Multi-step reaction with 19 steps 1.1: 75 percent / KOH / Heating 2.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C 2.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C 3.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C 4.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C 4.2: diethyl ether; petroleum ether / 1 h / -78 °C 5.1: 378 mg / triethylamine; methanesulfonyl chloride / CH2Cl2 / 4 h / 20 °C 6.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C 6.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C 6.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C 7.1: 91 percent / PCC / CH2Cl2 / 48 h / 20 °C 8.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 9.1: 173 mg / mCPBA / CH2Cl2 / 1 h / 0 °C 10.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 11.1: magnesium bromide diethyl etherate / CH2Cl2 / 12 h / -78 °C 12.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 13.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C 13.2: 77 percent / camphorsulfonic acid / CH2Cl2 / 18 h / 20 °C 14.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 15.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C 15.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C 16.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C 17.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C 17.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C 18.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 19.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

参考文献

Mohr, Peter J.; Halcomb, Randall L. Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1712 - 1713

501369-29-5

501369-39-7

反应条件

Multi-step reaction with 17 steps 1.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C 2.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C 2.2: diethyl ether; petroleum ether / 1 h / -78 °C 3.1: 378 mg / triethylamine; methanesulfonyl chloride / CH2Cl2 / 4 h / 20 °C 4.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C 4.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C 4.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C 5.1: 91 percent / PCC / CH2Cl2 / 48 h / 20 °C 6.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 7.1: 173 mg / mCPBA / CH2Cl2 / 1 h / 0 °C 8.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 9.1: magnesium bromide diethyl etherate / CH2Cl2 / 12 h / -78 °C 10.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 11.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C 11.2: 77 percent / camphorsulfonic acid / CH2Cl2 / 18 h / 20 °C 12.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 13.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C 13.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C 14.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C 15.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C 15.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C 16.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 17.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

参考文献

Mohr, Peter J.; Halcomb, Randall L. Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1712 - 1713

501369-33-1

501369-39-7

参考文献

Mohr, Peter J.; Halcomb, Randall L. Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1712 - 1713

89-82-7

501369-39-7

反应条件

Multi-step reaction with 20 steps 1.1: 70 percent / LDA; LiCl 2.1: 75 percent / KOH / Heating 3.1: diisopropyl amine; n-butyllithium; triethylamine / chlorotrimethylsilane / tetrahydrofuran; petroleum ether / -78 - 0 °C 3.2: bromine / tetrahydrofuran; petroleum ether / 2 h / -78 °C 4.1: 5.0 g / lithium carbonate; lithium bromide / dimethylformamide / 4 h / 100 - 105 °C 5.1: diisopropyl amine; n-butyllithium / diethyl ether; petroleum ether / 0.58 h / -78 °C 5.2: diethyl ether; petroleum ether / 1 h / -78 °C 6.1: 378 mg / triethylamine; methanesulfonyl chloride / CH2Cl2 / 4 h / 20 °C 7.1: lithium chloride / tetrahydrofuran / 2 h / 20 °C 7.2: n-butyllithium / tetrahydrofuran; petroleum ether / 0.08 h / -78 °C 7.3: 70 percent / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C 8.1: 91 percent / PCC / CH2Cl2 / 48 h / 20 °C 9.1: cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 10.1: 173 mg / mCPBA / CH2Cl2 / 1 h / 0 °C 11.1: 86 percent / Dess-Martin periodonane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 12.1: magnesium bromide diethyl etherate / CH2Cl2 / 12 h / -78 °C 13.1: 1.0 g / pyridine; trifluoroacetic anhydride; triethylamine / CH2Cl2 / 3.5 h / 0 - 20 °C 14.1: magnesium bromide diethyl etherate; butanethiol / diethyl ether / 15 h / 20 °C 14.2: 77 percent / camphorsulfonic acid / CH2Cl2 / 18 h / 20 °C 15.1: 94 percent / cerium trichloride; sodium borohydride / methanol / 0.5 h / 0 °C 16.1: triphenylphosphine; diethyl azodicarboxylate; 4-nitrobenzoic acid / tetrahydrofuran / 12 h / 20 °C 16.2: 86 percent / sodium methoxide / methanol / 1 h / 20 °C 17.1: 92 percent / imidazole / dimethylformamide / 2 h / 40 °C 18.1: t-butyllithium / diethyl ether; pentane / 0.5 h / -78 °C 18.2: 51 percent / TMEDA / diethyl ether; pentane / 0.08 h / -78 °C 19.1: 90 percent / Dess-Martin periodinane; sodium bicarbonate / CH2Cl2 / 1 h / 20 °C 20.1: TBAF / tetrahydrofuran / 0.5 h / 0 °C

参考文献

Mohr, Peter J.; Halcomb, Randall L. Journal of the American Chemical Society, 2003 , vol. 125, # 7 p. 1712 - 1713