Naturstoffchemie, 180. Synthese von Acronycinepoxid

Abstract

Natural Product Chemistry, 180. – Synthesis of Acronycine Epoxide Treatment of acronycine (1) with dimethyldioxirane in the presence of potassium carbonate resulted in acronycine epoxide (2), 1,2‐dihydro‐1,2‐dihydroxyacronycine and 5‐hydroxyacronycine (3).

2,2-dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties

“…Most of the attempts to improve the activity of acronycine by structural modifications have been focused on the modification on pyran moiety specially on 1,2-double bond by hydration (Mitaku et al, 1988), epoxidation (Reisch and Top, 1991;Reisch and Schiwek, 1994) or dihydroxylation (Elomri et al, 1996;Costes et al, 1999;Magiatis et al, 1999), substitution of 6-OCH 3 group by O-alkyl, O-alkenyl, and others (Schneider et al, 1972), and annulation of benzene ring on to ring-A (Costes et al, 2000;Nguyen et al, 2006). On the other hand, modifications of acronycine by introducing (a) substituent(s) on to ring-A are limited (Svododa, 1966;Svododa et al, 1966;Smolders et al, 1982;Smolders et al, 1984;Blechert et al, 1980;Reisch et al, 1993) only with very limited substituents.…”

Quinoline, quinazoline, and acridone alkaloids

“…Kokusagainine was mildly toxic in the brine shrimp toxicity assay (LC,, = 367 ppm), but flindersiamine showed no toxicity. tautomerization of which yields the 3-methylbuta-1,3-dienyl intermediate (69). This hypothetical compound gains credibility from the recent isolation of similar dienes by Greger and coworkers (see Section 2.3 above).…”