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Formal total synthesis of neocarzinostatin chromophore
Shoji Kobayashi1, Makiko Hori, Guang Xing Wang
1Department of Chemistry, Graduate Schools of Science, Tohoku University, Sendai 980-8578, Japan. koba@c.s.osakafu-u.ac.jp
Abstract:
[reaction: see text] An efficient route to the neocarzinostatin chromophore aglycon has been developed. The present strategy involves a stereoselective intramolecular acetylide-aldehyde cyclization to form the C5-C6 bond, followed by efficient installation of alpha-epoxide, naphthoate, and carbonate functionalities. The C8-C9-olefin was introduced by using the Martin sulfurane dehydration reaction to furnish the highly reactive aglycon.
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