Transition metal catalyzed reactions in organic synthesis, part VI. Cobalt mediated intramolecular [2+2+2]-cycloaddition of enediynes towards linear annelated polycycles

The cobalt mediated [2+2+2]-cycloaddition of enediynes 13 and 18 affords linear annelated polycycles such as the hexahydro naphthalene 14 and the decahydro anthracene 19. This latter compound can be transformed into the enantiomerically pure anthracene derivative 21 in only two reaction steps. 1,9,1...

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Bibliographic Details
Published inSynlett no. 14; pp. 2188 - 2192
Main Authors Eckenberg, P, Groth, U
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ONE-STEP CONSTRUCTION
annelated polycycles
FORMAL TOTAL-SYNTHESIS
2+2+2 CYCLOADDITION
(+/-)-STRYCHNINE
MOLECULES
<2&2&2>-CYCLOADDITIONS
ANTHRAQUINONES
FRAMEWORK
[2+2+2]-cycloaddition
TRICYCLIC DIENES
CYCLIZATION
enediynes
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Summary:The cobalt mediated [2+2+2]-cycloaddition of enediynes 13 and 18 affords linear annelated polycycles such as the hexahydro naphthalene 14 and the decahydro anthracene 19. This latter compound can be transformed into the enantiomerically pure anthracene derivative 21 in only two reaction steps. 1,9,10-Trihydroxy octahydro anthracene (21) represents the ABC-framework of many anthracycline antibiotics such as the antitumor active daunomycine.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-42088