Total synthesis of (-)-solanapyrone A via enzymatic Diels-Alder reaction of prosolanapyrone

被引：86

作者：

Oikawa, H ^{[1
]}

Kobayashi, T ^{[1
]}

Katayama, K ^{[1
]}

Suzuki, Y ^{[1
]}

Ichihara, A ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Agr, Dept Biosci & Chem, Sapporo, Hokkaido 060, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 24期

关键词：

D O I：

10.1021/jo980743r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

引用

页码：8748 / 8756

页数：9

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