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Chiral resolution of (±)-keramaphidin B and isolation of manzamine L, a new β-carboline alkaloid from a sponge Amphimedon sp.

1996; Elsevier BV; Volume: 52; Issue: 7 Linguagem: Inglês

10.1016/0040-4020(95)01057-2

1464-5416

Masashi Tsuda, Kenjiro Inaba, Naoko Kawasaki, Kaori Honma, Jun’ichi Kobayashi,

Chemical synthesis and alkaloids

Both enantiomers of keramaphidin B (1) were separated by using chiral HPLC, of which one may be a plausible biogenetic precursor of ircinals A (4) and B (5) and manzamines A (2) and B (3), while the other may be associated with antipodes of manzamine alkaloids such as ircinols A (6) and B (7). Isolation and structure elucidation of a new manzamine congener, manzamine L (8), and absolute configurations at C-1 of 8 and manzamines D (10) and H (9) deduced from the Cotton effects are also described.