Intramolecular Cyclization of (2-Functionalized Allyl)trimethylsilane with Acid Chloride. Synthesis of Two Guaianolide-Type α-Methylene γ-Lactones

α-Methylene γ -lactone fused to seven-membered carbocycle was synthesized by intramolecular cyclization of (2-ethoxycarbonylallyl)trimethylsilane or (2-acetoxymethylallyl)trimethylsilane with acid chloride. The former was found to be a better way for seven-membered carbocyclization, while the latter...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 74; no. 10; pp. 1947 - 1961
Main Authors Kuroda, Chiaki, Kobayashi, Kenichi, Koito, Akira, Anzai, Shuzo
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 01.10.2001
Chemical Soc Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
BETA-(ALKOXYCARBONYL)ALLYLSILANE
CONJUGATED DIENONES
SILICON-CONTAINING COMPOUNDS
14,15-DINOREUDESMANOLIDES
LEWIS-ACID
DITERPENOIDS
NATURAL SESQUITERPENOIDS
STEREOCHEMISTRY
ALLYLSILANES
ADDITIONS
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Summary:α-Methylene γ -lactone fused to seven-membered carbocycle was synthesized by intramolecular cyclization of (2-ethoxycarbonylallyl)trimethylsilane or (2-acetoxymethylallyl)trimethylsilane with acid chloride. The former was found to be a better way for seven-membered carbocyclization, while the latter method was applicable to the synthesis of α- methylene γ -lactones fused to eight- and fourteen-membered carbocycles. Both guaian-8,12- and 6,12-olide type of compounds were synthesized by this method, in which the cyclization reaction proceeded stereoselectively. It was also found that both (Z)- and (E)-allylsilanes afford the same stereoisomer as the major product.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.74.1947