Tetrahedron p. 10569 - 10582 (1996)
Update date:2022-08-04
Topics:
Rigby, James H.
Mateo, Mary E.
The total syntheses of (±)-α-lycorane and dehydroanhydrolycorine are described. The key intermediate in both approaches is the hydroindolone 5, prepared from the [1 + 4] cycloaddition reaction of 1-isocyanatocyclohexene and cyclohexyl isocyanide. Alkylation of 5 with arylbromide 6 afforded 7. Hydrolysis of enamide 7 followed by reduction of the resultant enol yielded 10 as a single diastereomer. Radical-based cyclization of this intermediate gave 11 possessing the requisite trans-fusion between rings B and C in good yield. Radical deoxygenation followed by reduction of the amide carbonyl function afforded (±)-α-lycorane. Similarly, alkylation of 5 with 6-(chloromethyl)-5-iodo-1,3-benzodioxole gave 14. Treatment of 14 with Pd(OAc)2 employing the Jeffery modification of the Heck reaction gave tetracycle 9. Hydrolysis of 9 followed by oxidation with DDQ afforded 15. Reduction of the two carbonyl functions in this material using lithium aluminum hydride afforded 4-hydroxyanhydrolycorine (16). Mesylation of the hydroxyl group led to rapid, spontaneous elimination producing anhydrodehydrolycorine.
View MoreShanghai Bojing Chemical Co., Ltd.
Contact:021-37122233
Address:6F Buildiing 11,No.388,Baifu Road,District Fengxian.Shanghai, China.
shijiazhuang alkay chemicals co..ltd(expird)
Contact:86-311-67692035
Address:2601,juntang building,qiaodong district,shijiazhuang
Shifang Taifeng New Flame Retardant Co., Ltd
Contact:02884721008
Address:tingjiang industrial park, hefeng town
Shanghai Witshoot Internet Technology Co Ltd
Contact:+86-21-66390020
Address:Room 419, No.285 Luochuan Road (E)
Shanghai Kangxin Chemical Co., Ltd
Contact:+86 21 60717227
Address:118,Ganbai Village,Waigang Town,Jiading District,Shanghai
Doi:10.1039/c5ob00472a
(2015)Doi:10.1016/S0040-4039(01)83177-4
(1977)Doi:10.1021/ja00498a023
(1979)Doi:10.1055/s-1977-24612
(1977)Doi:10.1246/bcsj.74.2433
(2001)Doi:10.1016/j.bmc.2005.06.039
(2005)