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  • Title: Enantioselective total synthesis of the antitumor macrolide rhizoxin D.
    Author: Lafontaine JA, Provencal DP, Gardelli C, Leahy JW.
    Journal: J Org Chem; 2003 May 30; 68(11):4215-34. PubMed ID: 12762720.
    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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