+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Synthesis of the phthalide isoquinoline alkaloids levo egenine levo corytensine and levo bicuculline by asymmetric carbonyl addition of chiral dipole stabilized organometallics



Synthesis of the phthalide isoquinoline alkaloids levo egenine levo corytensine and levo bicuculline by asymmetric carbonyl addition of chiral dipole stabilized organometallics



Journal of Organic Chemistry 56(4): 1564-1569



The asymmetric addition of metalated [(methylenedioxy)isoquinolyl]oxazolines is 100% selective for the erythro (.alpha.-hydroxybenzyl)isoquinoline diastereomers, with 2:1 selectivity of the two possible erythro stereoisomers. Enrichment to 100% ee after removal of the auxiliary and conversion to (-)-bicuculline and (+)-bicuculline diol establish the absolute configuration of the major addition product. Inversion of the C-9 hydroxyl affords entry into the threo series as well. The asymmetric carbonyl addition was used to synthesize, for the first time, the phthalide-isoquinoline hemiacetals corytensine and egenine, confirming the previously assigned structures and absolute configurations, and establishing the identity of egenine with decumbensine and of corytensine with epi-.alpha.-decumbensine.

Please choose payment method:






(PDF emailed within 1 workday: $29.90)

Accession: 007860258

Download citation: RISBibTeXText


Related references

General conjugate addition method for the synthesis of enantiomerically pure lignans total synthesis of levo and dextro burseran levo dehydroxycubebin levo trichostin levo cubebin levo 5 ethoxyhinokinin and levo hinokinin. Journal of Organic Chemistry 55(14): 4340-4349, 1990

Synthesis of levo egenine decumbensine by asymmetric carbonyl addition. Tetrahedron Letters 31(26): 3711-3714, 1990

Asymmetric synthesis of indole alkaloids from l tryptophan formal syntheses of levo koumine levo taberpsychine and levo koumidine. Tetrahedron Letters 32(31): 3895-3898, 1991

The conversion of levo and dextro dihydrocarvone into chiral intermediates for the synthesis of levo polygodial levo warburganal and levo muzigadial. Tetrahedron 45(5): 1447-1452, 1989

Asymmetric total synthesis of levo protoemetinol levo protoemetine levo emetine and levo tubulosine by highly stereocontrolled radical cyclizations. Journal of the Chemical Society Perkin Transactions I (5): 1469-1476, 1990

Enantiospecific total synthesis of the ajmaline related alkaloids levo suaveoline levo raumacline and levo n beta methylraumacline. Journal of the American Chemical Society 114(17): 6910-6912, 1992

Chiral formamidines the total asymmetric synthesis of levo 8 azaestrone and related levo 8 aza 12 oxo 17 deoxoestrone. Journal of Organic Chemistry 57(17): 4732-4740, 1992

Total synthesis of the lignans levo and dextro burseran levo cubebin and levo hinokinin by diastereoselective conjugate addition of benzyl anions to 2 r and s benzyloxy 2 5 dihydro 4 3 4 methylenedioxybenzoylfuran. Tetrahedron Letters: 3599-3602, 1988

Asymmetric synthesis 26. an expeditious enantioselective synthesis of the defense alkaloids levo euphococcinine and levo adaline via the cnr s method. Journal of Organic Chemistry 57(15): 4211-4214, 1992

Asymmetric synthesis of yohimban alkaloids total synthesis of levo pseudoyohimban and levo alloyohimban. Journal of Organic Chemistry 56(9): 2960-2964, 1991

Kinetics of oxidation of some alpha amino acids l levo arginine l levo histidine l dextro ornithine l levo tryptophan l levo threonine by sodium n chloro 4 methylbenzenesulfonamide chloramine t in alkaline medium. International Journal of Chemical Kinetics 17(7): 769-785, 1985

Biomimetic synthesis of levo deoxyrhexifoline levo tecostidine and levo actinidine by transformations of the iridoid glycoside loganin. Planta Medica 56(6): 535, 1990

Enantio controlled route to the furofuran lignans the total synthesis of levo sesamolin levo sesamin and levo acuminatolide. Journal of the Chemical Society Chemical Communications (3): 189-191, 1988

An enantioselective synthesis of levo 6 aza 6 carbethoxy 2 oxabicyclo levo 3.3.0 octan 3 one from s levo malic acid. Heterocycles 24(3): 641-646, 1986

Stereocontrolled synthesis of levo prezizanol levo prezizaene their epimers and levo allokhusiol. Tetrahedron 46(3): 761-774, 1990