An Improved Synthesis of Conduritol A |
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| Authors: | Richard C. Cambie Noel D. Renner Peter S. Rutledge Paul D. Woodgate |
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| Affiliation: | Department of Chemistry , University of Auckland , Auckland, New Zealand |
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| Abstract: | Recently Knapp and coworkers1 reported a highly stereoselective synthesis of the naturally occurring cyclitol conduritol A (1) from p-benzoquinone (2) in 39% overall yield using 9-[(benzyloxy)methoxy]-anthracene (3) as a protecting group (Scheme 1). Although regeneration of the olefinic bond in the product was achieved at room temperature via an oxyanion-accelerated2 retro Diels-Alder reaction, this step necessitated protection of the newly introduced groups. |
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