ISSN:
0947-3440
Keywords:
Michellamines
;
Korupensamines
;
Alkaloids, naphthylisoquinoline
;
Biaryls
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The biomimetic first total synthesis of michellamines A, B, and C (1a-c), naturally occurring quateraryl alkaloids with high anti-HIV activity, is described. Key precursors are the molecular “halves” of michellamines, the antimalarial naphthylisoquinoline alkaloids korupensamine A (2a) and B (2b), which are likewise natural products. These “monomeric” naphthylisoquinoline alkaloids were prepared by Stille-type intermolecular aryl coupling of the O-isopropyl-protected and trialkylstannyl-activated naphthalene building block 4b with the threefold benzyl-protected and brominated, enantiomerically pure tetrahydroisoquinoline building block 3a. Ultimate “dimerization” of the protected korupensamines was achieved by biomimetic oxidative phenolic coupling using silver(I) oxide, followed by deprotection to give authentic michellamines. This synthetic route should allow us to easily prepare a broad series of modified analogs of michellamines for extensive structure-activity investigations.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961215
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