The biomimetic first total synthesis of michellamines A, B, and C (la-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 0-isopropyl-protected and trialkylstannyl-activated naphthalene building block 4 b
Lo]Me OH Me OH l a OH Me Ib OH Me Me OH OH M Me ' O w M e \ N. " IC OH Medispose of four stereogenic centers and three biaryl axes, of which the two outer ones are stereogenic, whereas the inner one, which links the constitutionally identical molecular "halves", is conformatively unstable. The constitution and
The title compound was prepared from 1,4-dibromo-2,3-dihydroxynaphthalene by two-fold esterification with l-bromo-2-naphthoic acid. It crystallizes from chloroform in the triclinic sys tem, space group P 1; a = 1226.6(3), b = 1246.9(3), c = 1218.8(3) pm, a = 107.50°, ß = 90.94^, y = 113.56°. The asymmetric unit is described with a statistically disordered CHC13.
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