Total Synthesis of (±)-Meridinol, (±)-Epimeridinol, and a Related Cyclolignan

• Published in: Journal of natural products (Washington, D.C.) Vol. 56; no. 4; pp. 600 - 605
• Main Authors: Amer, Adel, Bauer, Frank, Zimmer, Hans
• Format: Journal Article
• Language: English
• Published: CINCINNATI American Chemical Society 01.04.1993; AMER SOC PHARMACOGNOSY; American Society of Pharmacognosy
• Subjects: AGENTES ANTINEOPLASTICOS; AMERICA CENTRAL; AMERICA DEL SUR; AMERIQUE CENTRALE; AMERIQUE DU SUD; ANTINEOPLASTIC AGENTS; CENTRAL AMERICA; Chemistry; Chemistry, Medicinal; Exact sciences and technology; EXTRACTOS VEGETALES; EXTRAIT D'ORIGINE VEGETALE; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Life Sciences & Biomedicine; LIGNINAS; LIGNINE; LIGNINS; MEDICAMENT CYTOSTATIQUE; MOLECULAR STRUCTURE; Organic chemistry; Pharmacology & Pharmacy; PLANT EXTRACTS; Plant Sciences; Preparations and properties; Science & Technology; SOUTH AMERICA; STRUCTURE; ZANTHOXYLUM; ZANTHOXYLUM FAGARA; NEOLIGNANS; LIGNANS; Five membered ring; Tertiary alcohol; Epimer; Bicyclic compound; Racemate; Lactone; Lignan; Aromatic compound; Tetracyclic compound; Oxygen heterocycle; Total synthesis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np50094a021

The naturally occurring lignan meridinol [5] was synthesized in a racemic form in a convergent manner involving a Grignard reaction on E-4-(3,4-methylenedioxybenzylidene)-2,3(2H,5H)-furandione [7]. The hitherto unknown epimeridinol [11] and the cyclolignan 15 were also prepared. The structure assignments of the synthesized lignans are determined by their spectroscopic data.