TOTAL SYNTHESIS OF (-)-GRAYANOTOXIN-III

被引：114

作者：

KAN, T ^{[1
]}

HOSOKAWA, S ^{[1
]}

NARA, S ^{[1
]}

OIKAWA, M ^{[1
]}

ITO, S ^{[1
]}

MATSUDA, F ^{[1
]}

SHIRAHAMA, H ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC SCI,DEPT CHEM,SAPPORO,HOKKAIDO 060,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 19期

关键词：

D O I：

10.1021/jo00098a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Total synthesis of(-)-grayanotoxin III (3), a unique tetracyclic diterpene isolated from the leaves of various plants of the family Ericaceae, has been successfully accomplished featuring the highly stereoselective cyclization reactions induced by SmI2.

引用

页码：5532 / 5534

页数：3

共 42 条

[21]

KITO M, 1993, SYNLETT, P158

[22]

KODAMA M, 1975, TETRAHEDRON LETT, P3065

[23] MECHANISM OF DIPHENYL DISULFIDE CATALYSIS OF THERMAL THIA-ALLYLIC REARRANGEMENT [J].

KWART, H ;

JOHNSON, NA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (17) :2855-2858

[24] OCCURRENCE OF PERMUTATIONAL ISOMERISM IN MECHANISM OF THERMAL THIA-ALLYLIC REARRANGEMENT [J].

KWART, H ;

JOHNSON, NA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) :3441-3449

[25] INTERMOLECULAR COUPLINGS BETWEEN VINYL TRIFLATES AND ALLYLIC CUPRATES - A MILD AND RAPID ATYPICAL ROUTE TO 1,4-DIENES [J].

LIPSHUTZ, BH ;

ELWORTHY, TR .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1695-1696

[26] THE CHEMISTRY OF HIGHER-ORDER ORGANOCUPRATES [J].

LIPSHUTZ, BH ;

WILHELM, RS ;

KOZLOWSKI, JA .

TETRAHEDRON, 1984, 40 (24) :5005-5038

[27]

LIPSHUTZ BH, 1987, SYNTHESIS-STUTTGART, P325

[28] A FORMAL SYNTHESIS OF APLASMOMYCIN - ASSEMBLY OF THE C3-C17 SEGMENT BASED ON 1,3-ASYMMETRIC AND 1,5-ASYMMETRIC REDUCTIONS [J].

MATSUDA, F ;

TOMIYOSHI, N ;

YANAGIYA, M ;

MATSUMOTO, T .

TETRAHEDRON, 1990, 46 (10) :3469-3488

[29] STEREOCONTROLLED SYNTHESIS OF D-PENTITOLS, 2-AMINO-2-DEOXY-D-PENTITOLS, AND 2-DEOXY-D-PENTITOLS FROM D-GLYCERALDEHYDE ACETONIDE [J].

MINAMI, N ;

KO, SS ;

KISHI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) :1109-1111

[30] APPLICATION OF LANTHANIDE REAGENTS IN ORGANIC-SYNTHESIS [J].

MOLANDER, GA .

CHEMICAL REVIEWS, 1992, 92 (01) :29-68

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