Asymmetric Total Syntheses and Structure Elucidations of (+)-Eurotiumide F and (+)-Eurotiumide G

• Published in: Chemical & pharmaceutical bulletin Vol. 67; no. 9; pp. 953 - 958
• Main Authors: Nakayama, Atsushi, Sato, Hideo, Nagano, Shuji, Karanjit, Sangita, Imagawa, Hiroshi, Namba, Kosuke
• Format: Journal Article
• Language: English; Japanese
• Published: TOKYO The Pharmaceutical Society of Japan 01.09.2019; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Absolute configuration; Asymmetry; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Crystallography; dihydropyran; Life Sciences & Biomedicine; natural product; Natural products; Pharmacology & Pharmacy; Phenolic compounds; Phenols; Physical Sciences; Science & Technology; Stereochemistry; total synthesis; DESMODIUM-CAUDATUM; dihydropyran; ETHERS; CARBONYLATION; natural product; DIHYDROISOCOUMARINS; PRENYLATED FLAVONOIDS; total synthesis; DERIVATIVES; SP; N-FORMYLSACCHARIN
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.c18-00948

Asymmetric total syntheses of dihydropyran containing natural products, (+)-eurotiumide F and (+)-eurotiumide G have been described. These total syntheses revealed the absolute configuration of eurotiumide F and G, and confirmed the reported structure of eurotiumide F and revised the reported structure of eurotiumide G. Highlight of these syntheses is thermal rearrangement with 4-methoxyisochroman-1-one derivative having propargyl ether on phenolic ether under thermal condition to construct dihydropyran ring. X-Ray crystallographic analysis of (+)-eurotiumide G clarified the stereochemistry at the C1-position.