Journal of the American Chemical Society p. 8107 - 8115 (1993)
Update date:2022-08-05
Topics:
Ihara, Masataka
Taniguchi, Takahiko
Makita, Kei
Takano, Michiko
Ohnishi, Masaru
Taniguchi, Nobuaki
Fukumoto, Keiichiro
Kabuto, Chizuko
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.
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