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

共 25 条

[11] SYNTHESIS OF (+)-SOLANAPYRONE-A
ICHIHARA, A
MIKI, M
TAZAKI, H
SAKAMURA, S
[J]. TETRAHEDRON LETTERS, 1987, 28 (11) : 1175 - 1178
[12] Ichihara A, 1998, CURR ORG CHEM, V2, P365
[13] ICHIHARA A, 1997, DYNAMIC ASPECTS NATU, P119
[14] AN IMPROVED PROCEDURE FOR THE PREPARATION OF THE DESS-MARTIN PERIODINANE
IRELAND, RE
LIU, LB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) : 2899 - 2899
[15] Enzymatic activity and partial purification of solanapyrone synthase: first enzyme catalyzing Diels-Alder reaction
Katayama, K
Kobayashi, T
Oikawa, H
Honma, M
Ichihara, A
[J]. BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1998, 1384 (02): : 387 - 395
[16] MANAS MM, 1984, SYNTHESIS-STUTTGART, P430
[17] FIRST DIRECT EVIDENCE IN BIOLOGICAL DIELS-ALDER REACTION OF INCORPORATION OF DIENE-DIENOPHILE PRECURSORS IN THE BIOSYNTHESIS OF SOLANAPYRONES
OIKAWA, H
SUZUKI, Y
NAYA, A
KATAYAMA, K
ICHIHARA, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) : 3605 - 3606
[18] STRUCTURE AND ABSOLUTE-CONFIGURATION OF SOLANAPYRONE-D - A NEW CLUE TO THE OCCURRENCE OF BIOLOGICAL DIELS-ALDER REACTIONS
OIKAWA, H
YOKOTA, T
ICHIHARA, A
SAKAMURA, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) : 1284 - 1285
[19] ENZYMATIC-ACTIVITY CATALYZING EXO-SELECTIVE DIELS-ALDER REACTION IN SOLANAPYRONE BIOSYNTHESIS
OIKAWA, H
KATAYAMA, K
SUZUKI, Y
ICHIHARA, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) : 1321 - 1322
[20] BIOSYNTHESIS OF SOLANAPYRONE-A, A PHYTOTOXIN OF ALTERNARIA-SOLANI
OIKAWA, H
YOKOTA, T
ABE, T
ICHIHARA, A
SAKAMURA, S
YOSHIZAWA, Y
VEDERAS, JC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) : 1282 - 1284

← 1 2 3 →