| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347422 | Tetrahedron: Asymmetry | 2009 | 6 Pages |
Concise syntheses of novel chiral pyrroloazacyclo and chiral tricyclic isoquinoline alkaloids, starting from the readily available (S)-1,2,3,4-tetrahydroisoquinoline carboxylic acid methyl ester, by utilizing cascade spiro-to fused and RCM protocols, are reported.
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(S)-Methyl 2-(4-diazo-5-ethoxy-3,5-dioxopentyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylateC18H21N3O5Ee > 97%[α]D=+5.8[α]D=+5.8 (c 0.65, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (3S)
(9R,9aS)-9a-Ethyl-9-methyl-1-oxo-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a] benzo[c]azepine-9,9a-dicarboxylateC18H21NO5Ee > 52%[α]D=-103.5[α]D=-103.5 (c 0.39, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (9R,9aS)
(9R,9aR)-9a-Ethyl-9-methyl-1-oxo-2,3,5,8,9,9a-hexahydro-1H-pyrrolo[1,2-a] benzo[c]azepine-9,9a-dicarboxylateC18H21NO5Ee > 40%[α]D=-31.4[α]D=-31.4 (c 0.16, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (9R,9aR)
(2aS,4aR,10bR)-10b-Hydroxymethyl-1,2,2a,4a,5,10,10b-heptahydro-3-oxa-10a-aza-benzo[e]-cyclopenta-[cd]azulene-4-oneC15H17NO3Ee > 97%[α]D=-35.4[α]D=-35.4 (c 0.20, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (2aS,9R,10bR)
(S)-Ethyl 2-diazo-3-oxo-5-[3-vinyl-3,4-dihydroisoquinolin-2(1H)-yl] pentanoateC18H21N3O3Ee > 97%[α]D=-21.8[α]D=-21.8 (c 0.63, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (3S)
(R,Z)-Ethyl 1-oxo-2.3.4,5,10,13,13a-heptahydro-1H-pyrrolo-benzo[c]-azonine-13a-carboxylateC18H21NO3Ee > 95%[α]D=-6.4[α]D=-6.4 (c 0.44, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (13aR)
(S)-2-[1-Oxo-propenyl]-3-vinyl-3,4-dihydroisoquinolin-2(1H)-ylC14H15NOEe > 97%[α]D=+56.4[α]D=+56.4 (c 0.37, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (3S)
(S)-2-[1-Oxo-butenyl]-3-vinyl-3,4-dihydroisoquinolin-2(1H)-ylC15H17NOEe > 97%[α]D=+52.9[α]D=+52.9 (c 0.46, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (3S)
(S)-2-[1-Oxo-4-pentenyl]-3-vinyl-3,4-dihydroisoquinolin-2(1H)-ylC17H19NOEe > 97%[α]D=+44.9[α]D=+44.9 (c 0.70, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (3S)
(S)-3,11,11a-Trihydro-6H-pyridino[1,2-b]isoquinolin-4-oneC13H13NOEe > 97%[α]D=-124.6[α]D=-124.6 (c 0.53, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (11aS)
(S)-3,4,12,12a-Tetrahydro-7H-azepino[1,2-b]isoquinolin-5-oneC14H15NOEe > 97%[α]D=+35.1[α]D=+35.1 (c 0.47, CHCl3)Source of chirality: (S)-1,2,3,4-tetrahydro isoquinoline carboxylic acidAbsolute configuration: (12aS)
