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Synthesis of the spiroacetal core of the cephalosporolide family of natural products |
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| Authors: | Orla C. Finch Daniel P. Furkert Margaret A. Brimble |
| Affiliation: | 1. School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland 1142, New Zealand;2. Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand |
| Abstract: | The synthesis of four possible stereoisomers of the spiroacetal core of the natural products cephalosporolides H and I and penisporolides A and B is described. The key steps involve the use of Sharpless asymmetric dihydroxylation to install the desired stereochemistry of the γ-lactone ring and an oxidative radical cyclisation to form the spiroacetal ring system. |
| Keywords: | Cross metathesis Sharpless asymmetric dihydroxylation Oxidative radical cyclisation Spiroacetals Cephalosporolides |
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