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Efficient synthesis of the taxane C ring by fragmentation reaction of a bicyclo[2.2.2]octane derivative

โœ Scribed by Yoshimasa Hirai; Takuya Suga; Hiroto Nagaoka

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
238 KB
Volume
38
Category
Article
ISSN
0040-4039

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Asymmetric sequential Michael reaction:
Asymmetric sequential Michael reaction: Synthesis of optically active bicyclo[2.2.2]octane derivatives
โœ Hiroto Nagaoka; Kaoru Kobayashi; Toshiaki Okamura; Yasuji Yamada ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 243 KB

The sequential Michael reaction of (S)-4,5-di-O-isopropylidenepent-2enoate la and lb with lithium enolate 2 afforded diastereo-and enantioselec--tively bicyclo[2.2.2]octane 2 and 6 (or 51, respectively. The adducts were efficiently converted into both enantiomeric keto aldehydes c-j-7 and (+)-I. Bic