ACETOGENIC ISOQUINOLINE ALKALOIDS .66. FIRST TOTAL SYNTHESIS OF KORUPENSAMINE-A AND KORUPENSAMINE-B

Authors
BRINGMANN G GOTZ R KELLER PA WALTER R HENSCHEL P SCHAFFER M STABLEIN M KELLY TR BOYD MR
Citation
G. Bringmann et al., ACETOGENIC ISOQUINOLINE ALKALOIDS .66. FIRST TOTAL SYNTHESIS OF KORUPENSAMINE-A AND KORUPENSAMINE-B, Heterocycles, 39(2), 1994, pp. 503-508
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
39
Issue
2
Year of publication
1994
Pages
503 - 508
Database
ISI
SICI code
0385-5414(1994)39:2<503:AIA.FT>2.0.ZU;2-G
Abstract
The first total synthesis of korupensamines A (1a) and B (1b), highly polar naphthylisoquinoline alkaloids and, simultaneously, 'monomeric b uilding blocks' of the michellamines, is described. Key step is the Pd -II catalyzed intermolecular biaryl coupling of the two appropriately protected naphthalene and isoquinoline moieties (10) and (11), with th e coupling positions activated by bromine and trialkylstannane substit uents respectively.