A concise route to the right wing of ciguatoxin |
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Authors: | Atsushi TatamiMasayuki Inoue Hisatoshi UeharaMasahiro Hirama |
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Affiliation: | Department of Chemistry, Graduate School of Science, Tohoku University, and SORST, Japan Science and Technology Corporation (JST), Sendai 980-8578, Japan |
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Abstract: | A concise route to the HIJKLM-ring fragment 10 of ciguatoxin (CTX) and 51-hydroxyCTX3C was developed in which oxiranyl anion addition and intramolecular carbonyl olefination were utilized as key transformations. The present procedure requires only 23 steps from the I-ring 5, while 35 steps were employed in a previous synthesis of the corresponding right wing 11 of CTX3C. The high efficiency of the present synthesis ensures a supply of 10 for total synthesis and biomedical applications. |
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Keywords: | convergent synthesis intramolecular carbonyl olefination low-valent titanium complex polyether ciguatoxin 51hydroxy-CTX3C |
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