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A concise route to the right wing of ciguatoxin

✍ Scribed by Atsushi Tatami; Masayuki Inoue; Hisatoshi Uehara; Masahiro Hirama


Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
302 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis


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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