Nakayama Atsushi, Sato Hideo, Nagano Shuji, Karanjit Sangita, Imagawa Hiroshi, Namba Kosuke
Graduate School of Pharmaceutical Sciences, Tokushima University.
Faculty of Pharmaceutical Sciences, Tokushima Bunri University.
Chem Pharm Bull (Tokyo). 2019;67(9):953-958. 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.
已报道了含二氢吡喃的天然产物（+）-曲霉酰胺F和（+）-曲霉酰胺G的不对称全合成。这些全合成揭示了曲霉酰胺F和G的绝对构型，证实了已报道的曲霉酰胺F的结构，并修正了已报道的曲霉酰胺G的结构。这些合成的亮点是在热条件下，使具有炔丙基醚的4-甲氧基异色满-1-酮衍生物在酚醚上进行热重排以构建二氢吡喃环。（+）-曲霉酰胺G的X射线晶体学分析阐明了C1位的立体化学。
