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Total Synthesis of (±)-Hirsutene via Pd-Promoted Cycloalkenylation Reaction |
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| Authors: | Masahiro Toyota Youichi Nishikawa Kayoko Motoki Naomi Yoshida Keiichiro Fukumoto |
| Institution: | Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan |
| Abstract: | Beginning with trans-2-methyl-4-cyclohexenecarboxylic acid (9), a total synthesis of linear triquinane sesquiterpene (±)-hirsutene (1) has been accomplished. An acid catalyzed intramolecular conjugate addition (7→6a) and a Pd2+-promoted highly stereocontrolled cyclization (5→4) were utilized for the key step of the sequence. Interestingly, some synthetic intermediates exhibited cytotoxicity. |
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