Syntheses of strychnos and aspidospermatan-type alkaloids .8. Selective total syntheses of mossambine and 14-epi-mossambine by a radical cyclization reaction

被引：41

作者：

Kuehne, ME

Wang, TS

Seraphin, D

机构：

[1] Department of Chemistry, University of Vermont, Burlington

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 22期

关键词：

D O I：

10.1021/jo961023s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mossambine (6) was obtained by a six-step reaction sequence from the indoloazepine ester 7. Radical cyclization of the tetracyclic vinyl iodide 12a provided a racemic pentacyclic ketone 16E, which could be converted to either enantiomer by condensation with (S or R)-N,S-dimethyl-S-phenylsulfoximine and selective pyrolysis of the resulting diastereomeric alcohols 18 and 19 or 20 and 21. Selective reductions of the resolved (or racemic) ketone 16E provided mossambine (6) and its hydroxy epimer 17.

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页码：7873 / 7881

页数：9

相关论文

共 27 条

[1] STUDIES ON THE SYNTHESIS OF STRYCHNOS INDOLE ALKALOIDS - SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE [J].

BONJOCH, J ;

SOLE, D ;

BOSCH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :11017-11018

[2]

Bosch J., 1996, ALKALOIDS, V48, P75

[3] A STEREOSPECIFIC TOTAL SYNTHESIS OF ALPHA-SANTALOL [J].

COREY, EJ ;

KIRST, HA ;

KATZENEL.JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (21) :6314-&

[4] RAPID ACCESS TO THE HIGHLY OXYGENATED ASPIDOSPERMA ALKALOIDS VINDOLINE, VINDOROSINE, AND CATHOVALINE [J].

DANIELI, B ;

LESMA, G ;

PALMISANO, G ;

RIVA, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (14) :909-911

[5] ASPIDOSPERMA ALKALOIDS VIA CYCLIZATION OF SECODINE INTERMEDIATE - SYNTHESIS OF (+/-)-3-OXOVINCADIFFORMINE ETHYL-ESTER [J].

DANIELI, B ;

LESMA, G ;

PALMISANO, G ;

PASSARELLA, D ;

SILVANI, A .

TETRAHEDRON, 1994, 50 (23) :6941-6954

[6] REACTION OF ORGANOTIN HYDRIDES WITH ACETYLENIC ALCOHOLS [J].

ENSLEY, HE ;

BUESCHER, RR ;

LEE, K .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) :404-408

[7] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .22. NEW APPROACH TO STRYCHNOS ALKALOIDS - STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE [J].

FEVIG, JM ;

MARQUIS, RW ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5085-5086

[8]

Johnson C. R., 1985, ALDRICHIM ACTA, V18, P3

[9] N,S-DIMETHYL-S-PHENYLSULFOXIMINE - A REAGENT FOR THE OPTICAL RESOLUTION OF KETONES [J].

JOHNSON, CR ;

ZELLER, JR .

TETRAHEDRON, 1984, 40 (08) :1225-1233

[10] REACTION OF BENZENESELENINYL CHLORIDE WITH OLEFINS IN THE PRESENCE OF A LEWIS ACID - A NOVEL ONE-STEP VINYLIC CHLORINATION [J].

KAMIGATA, N ;

SATOH, T ;

YOSHIDA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (02) :449-454