Biosynthesis of lythraceae alkaloids: incorporation of DL-[4,5-13C2,6-14C]lysine and cis- and trans-4-(3,4-dihydroxyphenyl)-quinolizidin-2-one into vertine and lythrine

Abstract

DL-[4,5-13C2,6-14] Lysine is incorporated specifically, and via a symmetrical intermediate, into ring A of vertine (3) and lythrine (6); the cis- and trans-quinolizidinones, (9) and (10), are respectively and specifically, effective precursors for (3) and (6), and the corresponding mono-O-methyl ethers (11)–(14) are not utilized for alkaloid biosynthesis.