Enantioselective total synthesis of the antitumor macrolide rhizoxin D |
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Authors: | Lafontaine Jennifer A Provencal David P Gardelli Cristina Leahy James W |
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Institution: | Department of Chemistry, University of California, Berkeley 94720-1460, USA. |
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Abstract: | The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The C(1)-C(9) fragment of the molecule was synthesized utilizing a threefold pseudosymmetric intermediate ultimately derived from gamma-butyrolactone. The central core of rhizoxin D was prepared via a chiral resolution/asymmetric aldol protocol. Several methods for the generation of the polyene fragment were explored, and the side-chain was ultimately prepared from serine in six steps. The unification of the left and right wings of the molecule was achieved using a one-step olefination protocol, and the macrocyclization was carried out using a Horner-Emmons olefination at the C(2)-C(3) olefin. |
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