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Total Synthesis of (.+-.)-Tanikolide (IX)

✍ Scribed by Ruzhou Zhang; Zhiqin Wang; Fengping Wei; Yongren Huang

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 33
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.200245218

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Asymmetric transformations of 1,1-disubstituted alkenes provide important building blocks for chemical synthesis, but are often plagued with low stereoselectivities because it can be difficult for a chiral reagent or catalyst to discriminate between the enantiotopic faces of these substrates. [1] Am

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## Abstract The δ‐lactone‐containing natural product (+)‐tanikolide, a brine shrimp toxin and antifungal compound, was synthesized in nine steps with an overall yield of 26.4 % by employing Sharpless asymmetric epoxidation and ZrCl~4~‐catalyzed intramolecular acetalization as the key steps. The nov