169898-17-3Relevant academic research and scientific papers
Enantioselective total synthesis of the antitumor macrolide rhizoxin D
Lafontaine, Jennifer A.,Provencal, David P.,Gardelli, Cristina,Leahy, James W.
, p. 4215 - 4234 (2007/10/03)
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 γ-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.
Rhizoxin synthetic studies. 2. Synthesis of the left hand [C(10) to C(19)] and polyene fragments
Provencal, David P.,Gardelli, Cristina,Lafontaine, Jennifer A.,Leahy, James W.
, p. 6033 - 6036 (2007/10/02)
The syntheses of the central core and the polyene fragments of the antitumor macrolide rhizoxin have been achieved in an efficient manner. The core has been prepared in enantiopure form via a asymmetric allylation/aldol protocol. The selective oxidation o
