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

• Published in: Tetrahedron Vol. 52; no. 7; pp. 2319 - 2324
• Main Authors: Tsuda, Masashi, Inaba, Kenjiro, Kawasaki, Naoko, Honma, Kaori, Kobayashi, Jun'ichi
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 12-02-1996
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/0040-4020(95)01057-2

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.
This paper describes chiral resolution of (±)-keramaphidin B (
1), isolation and structure elucidation of a new manzamine congener, manzamine L (
8), and a plausible biogenetic path of manzamines A and B.