- Chemoenzymatic preparation of functionalized bicyclo[3.2.1]octenone and practical utilization
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A practical route for the synthesis of both enantiomers of a functionalized bicyclo[3.2.1]octenone, which is potentially useful as a versatile chiral building block, has been developed from 1,4-cyclohexanedione monoethylene acetal by employing proline-cat
- Ito, Shinichiro,Tosaka, Ayako,Hanada, Keisuke,Shibuya, Masatoshi,Ogasawara, Kunio,Iwabuchi, Yoshiharu
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p. 176 - 185
(2008/09/19)
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- Organocatalytic entry to chiral bicyclo[3.n.1]alkanones via direct asymmetric intramolecular aldolization
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(Chemical Equation Presented) The facile stereoselective syntheses of endo-8-hydroxybicyclo[3.3.1]nonan-2-one and encto-7-hydroxybicyclo[3.2.1]octan- 2-one, featuring an α-amino acid catalyzed intramolecular aldolization of σ-symmetric substrates, are des
- Itagaki, Noriaki,Kimura, Mari,Sugahara, Tsutomu,Iwabuchi, Yoshiharu
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p. 4185 - 4188
(2007/10/03)
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- Synthesis of polycyclic cyclobutane derivatives by tandem intramolecular Michael-aldol reaction under two complementary conditions: TBDMSOTf-Et3N and TMSI-(TMS)2NH
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The treatment of αβ-unsaturated esters having a ketone function at an appropriate position with either TBDMSOTf in the presence of Et3N or TMSI in the presence of (TMS)2NH provided, via a tandem intramolecular Michael-aldol reaction sequence, several different types of cyclobutane derivatives. The two reaction conditions were complementary. Tricyclo[4.2.1.03,8]nonanes 34 and 55, tricyclo[5.1.104,8]nonane 40, tricyclo[5.4.0.03,7]undecane 51, tetracyclo[5.4.0.03,7.09,11]undecane 45, and the bicyclo[3.2.0]heptanes 56, 57, and 58, which have structures either partially or completely similar to those of endiandric acids A (1a), B (1b), and C (2), trihydroxydecipiadiene (3), lintenone (4), italicene (5), and filifolone (6), were stereoselectively synthesized by the tandem reaction.
- Ihara, Masataka,Taniguchi, Takahiko,Makita, Kei,Takano, Michiko,Ohnishi, Masaru,Taniguchi, Nobuaki,Fukumoto, Keiichiro,Kabuto, Chizuko
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p. 8107 - 8115
(2007/10/02)
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