Mikaela DiBello, Zhi Xu, Alexandria M. Palazzo, Seth B. Herzon
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引用次数: 0
Abstract
We describe a stereoselective synthesis of the dimeric diazofluorene 15, a potential precursor to the cytotoxic C2-symmetric bacterial metabolite (−)-lomaiviticin A (1). An efficient route was developed to convert the tetracyclic diol 5 to the diketone 4 (five steps, 30% overall). Oxidative dimerization of the enoxysilane 14 provided the C2-symmetric dimeric diazofluorene 15 in 56% yield and with 15:1:0 diastereoselectivity. Deprotection and 2D NMR analysis indicated that the major diastereomer possessed the (2S,2′S) configuration found in 1. This approach may ultimately be useful in the synthesis of 1 itself.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.