A Novel Oxidative Intramolecular [4+2]Cycloaddition of Silylene-Protected Dihydroxystyrene Derivatives Leading to peri-Hydroxy Polycyclic Aromatic Compounds : A Synthesis of the ABCD Ring System of Frederucamycin A

Heating of the silylene protected dihydroxystyrene generated from the O-hydroxyacetophenone (3a) at 130-150°C for 15-48h in a sealed tube gave intramolecular [4+2]cycloaddition products (5 and 6). The addition of chloranil to the reaction mixture brought about an oxidative intramolecular [4+2]cycloa...

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Published inChemical and Pharmaceutical Bulletin Vol. 39; no. 8; pp. 2106 - 2114
Main Authors KITA, Yasuyuki, OKUNAKA, Ryuichi, HONDA, Takao, KONDO, Maiko, TAMURA, Osamu, TAMURA, Yasumitsu
Format Journal Article
LanguageEnglish
Published The Pharmaceutical Society of Japan 25.08.1991
Subjects
fredericamycin A
intramolecular [4+2]cycloaddition
oxidative cycloaddition
peri-hydroxy polycyclic aromatic compound
silylene derivative
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Abstract Heating of the silylene protected dihydroxystyrene generated from the O-hydroxyacetophenone (3a) at 130-150°C for 15-48h in a sealed tube gave intramolecular [4+2]cycloaddition products (5 and 6). The addition of chloranil to the reaction mixture brought about an oxidative intramolecular [4+2]cycloaddition to give the linearly condensed peri-hydroxy aromatic compound(7a) in excellent yield. The generality of this cycloaddition and application to a short and efficient synthesis of the ABCD ring system of fredericamycin A are described.
AbstractList Heating of the silylene protected dihydroxystyrene generated from the O-hydroxyacetophenone (3a) at 130-150°C for 15-48h in a sealed tube gave intramolecular [4+2]cycloaddition products (5 and 6). The addition of chloranil to the reaction mixture brought about an oxidative intramolecular [4+2]cycloaddition to give the linearly condensed peri-hydroxy aromatic compound(7a) in excellent yield. The generality of this cycloaddition and application to a short and efficient synthesis of the ABCD ring system of fredericamycin A are described.
Author KITA, Yasuyuki
KONDO, Maiko
TAMURA, Yasumitsu
HONDA, Takao
OKUNAKA, Ryuichi
TAMURA, Osamu
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SubjectTerms fredericamycin A
intramolecular [4+2]cycloaddition
oxidative cycloaddition
peri-hydroxy polycyclic aromatic compound
silylene derivative
Title A Novel Oxidative Intramolecular [4+2]Cycloaddition of Silylene-Protected Dihydroxystyrene Derivatives Leading to peri-Hydroxy Polycyclic Aromatic Compounds : A Synthesis of the ABCD Ring System of Frederucamycin A
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