The enantiocontrolled synthesis of (-)-tricholomenyn A, a novel antimitotic enynylcyclohexenone from Tricholoma acerbum

被引：36

作者：

Kamikubo, T ^{[1
]}

Ogasawara, K ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 14期

关键词：

D O I：

10.1039/cc9960001679

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(-)-Tricholomenyn A, a structurally novel antimitotic enynylcyclohexenone from Tricholoma acerbum, is synthesized in an enantiocontrolled manner from a chiral synthon of cis-1,4-dihydroxycyclohexa-2,5-diene and verifies the relative and the absolute structures of the natural product.

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页码：1679 / 1680

页数：2

相关论文

共 20 条

[1] SIMPLE AND DIRECT SYNTHESIS OF TRANS-1,2-BIS(TRI-NORMAL-BUTYLSTANNYL)ETHYLENE [J].

BOTTARO, JC ;

HANSON, RN ;

SEITZ, DE .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (25) :5221-5222

[2] TOTAL SYNTHESIS OF (+/-)-GINKGOLIDE-B [J].

COREY, EJ ;

KANG, M ;

DESAI, MC ;

GHOSH, AK ;

HOUPIS, JN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :649-651

[3] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[4] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[5]

GARLASCHELLI L, 1995, TETRAHEDRON LETT, V36, P5633

[6] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].

GEMAL, AL ;

LUCHE, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459

[7] MODIFIED STILLE COUPLING UTILIZING ALPHA-IODOENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW .

TETRAHEDRON LETTERS, 1992, 33 (07) :919-922

[8] DIRECT ALPHA-IODINATION OF CYCLOALKENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW ;

WOVKULICH, PM ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1992, 33 (07) :917-918

[9] Stereo- and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, via catalytic asymmetrization of a meso substrate [J].

Kamikubo, T ;

Hiroya, K ;

Ogasawara, K .

TETRAHEDRON LETTERS, 1996, 37 (04) :499-502

[10] THE ENANTIODIVERGENT TOTAL SYNTHESIS OF NATURAL AND UNNATURAL ENANTIOMERS OF THEOBROXIDE [J].

KAMIKUBO, T ;

OGASAWARA, K .

TETRAHEDRON LETTERS, 1995, 36 (10) :1685-1688