Studies on the synthesis of the core structures of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin

The bicyclo[7.3.0]dodecadiyne core structure of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin can be readily constructed by an intramolecular aldol reaction to form the C-8 C-9 bond only if the C-6,7 triple bond is complexed as its η 2Co 2(CO) 6-acetylene adduct. The bic...

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Bibliographic Details
Published inTetrahedron Vol. 52; no. 18; pp. 6283 - 6306
Main Authors Magnus, Philip, Carter, Rich, Davies, Martin, Elliott, Jason, Pitterna, Thomas
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.04.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTIBIOTIC NEOCARZINOSTATIN
ORGANIC-SYNTHESIS
CALICHEAMICIN-GAMMA-1
ACTIVATION
DNA
CHROMOPHORE-A
CHEMISTRY
ENEDIYNE
DICOBALT HEXACARBONYL-COMPLEX
MEDIATED ALDOL REACTION
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Summary:The bicyclo[7.3.0]dodecadiyne core structure of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin can be readily constructed by an intramolecular aldol reaction to form the C-8 C-9 bond only if the C-6,7 triple bond is complexed as its η 2Co 2(CO) 6-acetylene adduct. The bicyclo[7.3.0]dodecadiyne core structure of the antitumor agents neocarzinostatin, kedarcidin, C-1027 and maduropeptin can be readily constructed by an intramolecular aldol reaction. For example treatment of 1 with n-Bu 2BOTf/Et 3N/CH 2Cl 2 gave 2 (82%).
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00283-9