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A Vicinal Diol Approach for the Total Synthesis of Molestin E,ent-Sinulacembranolide A and ent-Sinumaximol A |
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| Authors: | Dr. Oskar Hoff Dr. Nicolas Kratena Daniya Aynetdinova Dr. Kirsten E. Christensen Prof. Timothy J. Donohoe |
| Affiliation: | 1. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA UK These authors contributed equally to this work;2. Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA UK |
| Abstract: | In this work an approach for the synthesis of furanocembranoid natural products containing the C-7,8-diol moiety is disclosed. This culminated in the first total synthesis of the natural product molestin E, together with ent-sinulacembranolide A and ent-sinumaximol A as well as a thorough exploration of their chemistry. Late-stage ring-closure of the C-7,8-diols to the corresponding epoxides was also demonstrated. Key features of this synthetic strategy include a stereoselective Baylis-Hillman reaction, ring-closing metathesis and Shiina macrolactonisation. Chiral-pool materials were deployed to ensure the desired absolute stereochemistry which was confirmed by late-stage single crystal X-ray diffraction. |
| Keywords: | cembranoids macrolactones metathesis natural products total synthesis |