Syntheses of Strychnos and Aspidospermatan-Type Alkaloids. 8. Selective Total Syntheses of Mossambine and 14-epi-Mossambine by a Radical Cyclization Reaction1
Authors:
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (22) , 7873-7881
Abstract
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 16 E, 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 16 E provided mossambine (6) and its hydroxy epimer 17.Keywords
This publication has 23 references indexed in Scilit:
- Studies on the Synthesis of Strychnos Indole Alkaloids. Synthesis of (.+-.)-DehydrotubifolineJournal of the American Chemical Society, 1995
- Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 7. Total Syntheses of Lagunamine, Isolagunamine, Condylocarpine, and IsocondylocarpineThe Journal of Organic Chemistry, 1995
- Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 6. Total Syntheses of (.+-.)-Echitamidine, (.+-.)-Alstogustine, (.+-.)-19-epi-Alstogustine, and (.+-.)-AkuammicineThe Journal of Organic Chemistry, 1994
- Syntheses of Strychnos- and Aspidospermatan-Type Alkaloids. 5. Total Syntheses of (.+-.)-Echitamidine and 20-epi- and 19-epi-20-epi-EchitamidineThe Journal of Organic Chemistry, 1994
- Total synthesis of strychnan and aspidospermatan alkaloids. 3. The total synthesis of (.+-.)-strychnineThe Journal of Organic Chemistry, 1993
- Formation of D-nor aspidosperma alkaloids by condensation of Nb-benzylindoloazepine with aldehydesThe Journal of Organic Chemistry, 1993
- Total syntheses of tubotaiwine and 19,20-dihydro-20-epi-akuammicineThe Journal of Organic Chemistry, 1991
- Biomimetic syntheses of indole alkaloids. 11. Syntheses of .beta.-carboline and indoloazepine intermediatesThe Journal of Organic Chemistry, 1985
- Studies in biomimetic alkaloid syntheses. 6. Alternative pathways to secodines and their acyclic enamino acrylate analogs. Total syntheses of desethylibophyllidine, D-norvincadifformine, desethylvincadifformine, 20-methyldesethylvincadifformine, and 3-oxovincadifformineThe Journal of Organic Chemistry, 1981
- Preparation of vinylene diacetateThe Journal of Organic Chemistry, 1981