THE ACID-CATALYZED REARRANGEMENT AND ABSOLUTE STEREOCHEMISTRY OF ISOSPONGIAQUINONE

被引：27

作者：

CAPON, RJ

机构：

[1] Department of Organic Chemistry, University of Melbourne, Parkville

来源：

JOURNAL OF NATURAL PRODUCTS | 1990年 / 53卷 / 03期

关键词：

D O I：

10.1021/np50069a042

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Chemical correlation has confirmed the marine natural product isospongiaquinone [3] to be the endocyclic double bond isomer of ilimaquinone [2]. Acid-catalyzed cyclization of both 3 and 2 yielded a common product 4 formed via phenolic addition to an isolable tetrasubstituted olefinic intermediate 6. © 1990, American Chemical Society. All rights reserved.

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页码：753 / 756

页数：4

相关论文

共 12 条

[1] A REVISION OF THE ABSOLUTE STEREOCHEMISTRY OF ILIMAQUINONE [J].

CAPON, RJ ;

MACLEOD, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :5059-5060

[2] STRUCTURAL AND STEREOCHEMICAL STUDIES ON MARINE NORTERPENE CYCLIC PEROXIDES .2. [J].

CAPON, RJ ;

MACLEOD, JK .

JOURNAL OF NATURAL PRODUCTS, 1987, 50 (02) :225-229

[3]

deRosa S., 1976, J CHEM SOC P1, P1408

[4] SOME METABOLITES OF THE MARINE SPONGES SMENOSPONGIA-AUREA AND SMENOSPONGIA (=POLYFIBROSPONGIA) ECHINA [J].

DJURA, P ;

STIERLE, DB ;

SULLIVAN, B ;

FAULKNER, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (08) :1435-1441

[5] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1988, 5 (06) :613-663

[6] INTERESTING ASPECTS OF MARINE NATURAL-PRODUCTS CHEMISTRY [J].

FAULKNER, DJ .

TETRAHEDRON, 1977, 33 (12) :1421-1443

[7] MARINE NATURAL-PRODUCTS - METABOLITES OF MARINE-INVERTEBRATES [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1984, 1 (06) :551-598

[8] NEW QUINONES FROM A DICTYOCERATID SPONGE [J].

KAZLAUSKAS, R ;

MURPHY, PT ;

WARREN, RG ;

WELLS, RJ ;

BLOUNT, JF .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (12) :2685-2697

[9]

LUDIBRAND RT, 1979, TETRAHEDRON, V35, P609

[10]

MINALE L, 1974, Tetrahedron Letters, V38, P3401