ORGN 624 |
| Several 2, 11-cyclized cembranoids (eleutherobin, sclerophytin, astrogorgin, etc) possess potent antimitotic and/or anticancer activity. The promising biological activity of these diterpenoids suggests the need for further exploration of this family of natural products. We have developed a concise synthesis of the isobenzofuran bicycle common to most of the eunicellin diterpenes. We are employing the same strategy in an approach to analogs containing the isobenzofuran nucleus. A novel cycloaldol approach developed in our laboratory was used to build the hydroisobenzofuran core from readily available (S)-(+)-carvone. The isobenzofuran scaffold contains two points of diversity in the C9 ester and the bromoarene. We are investigating the use of a sulfonylhydrazone as a solid phase linker. Cleavage from the support will involve an allylic diazene rearrangement. The allylic diazene rearrangement sequence and the advantages of sulfonylhydrazone functional group as a potential versatile linker for solution and solid phase synthesis will be discussed.
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New Reactions and Methodology
8:00 AM-12:00 PM, Wednesday, 16 March 2005 Convention Center -- Ballroom 20 C-D, Oral
Division of Organic Chemistry |
