SYNTHETIC APPROACH TO APHIDICOLAN AND STEMODAN BASIC SKELETONS USING A TANDEM PRINCIPLE [2+2+2] AND [4+2] CYCLOADDITION REACTIONS

被引：12

作者：

STAMMLER, R ^{[1
]}

HALVORSEN, K ^{[1
]}

GOTTELAND, JP ^{[1
]}

MALACRIA, M ^{[1
]}

机构：

[1] UNIV PARIS 06,CNRS,CHIM ORGAN SYNTH LAB,F-75252 PARIS 05,FRANCE

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 03期

关键词：

D O I：

10.1016/0040-4039(94)85068-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy based upon the ''Tandem Principle'' : coupling of the cobalt catalyzed [2 + 2 + 2] cycloaddition and an intramolecular [4 + 2] Diels-Alder reaction allowed the formation of the stemodan skeleton in 11 high yield steps starring from C-ethoxycarbonyl cyclohexanone.

引用

页码：417 / 420

页数：4

共 13 条

[1] STEREOSELECTIVE ACCESS TO THE BASIC SKELETON OF TETRACYCLIC DITERPENES VIA A SEQUENCE OF CONSECUTIVE [3+2],[2+2+2], AND [4+2] CYCLOADDITION REACTIONS
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[4] ONE-STEP CONSTRUCTION OF THE STEMODANE FRAMEWORK VIA THE COBALT-CATALYZED CYCLIZATION OF MONOCYCLIC ENYNES - A FORMAL TOTAL SYNTHESIS OF STEMODIN
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[7] STEREOSPECIFIC DICOBALT OCTACARBONYL MEDIATED ENYNE CYCLIZATION FOR THE SYNTHESIS OF THE CYTOTOXIC SESQUITERPENE (+/-)-QUADRONE
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[8] STRUCTURES OF STEMODIN AND STEMODINONE
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) : 2705 - 2706
[9] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE
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[10] MILLER JA, 1983, SYNTHESIS-STUTTGART, P128

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