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Enantiocontrolled Construction of Functionalized Tetrahydrofurans:  Total Synthesis of (6S,7S,9R,10R)-6,9-Epoxynonadec-18-ene-7,10-diol, a Marine Natural Product

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journal contribution
posted on 18.02.1998, 00:00 by Zhi-Min Wang, Ming Shen
An efficient strategy has been developed for the construction of highly functionalized tetrahydrofurans. The key feature involves the use of Sharpless asymmetric dihydroxylation and the choice of a new bis-C3 building block 5 as the starting material which increased the efficiency. On the basis of this methodology, a marine natural product, (6S,7S,9R,10R)-6,9-epoxynonadec-18-ene-7,10-diol (1), was successfully synthesized in high enantioselectivity.