139630-91-4Relevant articles and documents
Enantioselective Total Synthesis of Didesepoxyrhizoxin
Kende, Andrew S.,Blass, Benjamin E.,Henry, James R.
, p. 4741 - 4744 (1995)
The first synthesis of the antitumor macrolide didesepoxyrhizoxin is described.
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.
Intramolecular palladium(II)-mediated alkoxy carbonylation as a route to functionalized tetrahydropyrans. synthesis of the C9-C32 segment of phorboxazole A
White, James D.,Kranemann, Christian L.,Kuntiyong, Punlop
, p. 4003 - 4006 (2007/10/03)
matrix presented Hydroxy alkene 12, synthesized stereoselectively from 2-methyloxazole-4-carboxaldehyde, underwent intramolecular methoxy carbonylation in the presence of palladium(II) acetate to give 13 in which all five stereogenic centers around the tetrahydropyran correspond to those in ring C of phorboxazole A. Aldehyde 15, derived from 13, was linked to hydroxy alkene 23 via a Wittig coupling, and the composite 25 was subjected to a second palladium(II) acetate mediated methoxy carbonylation to yield 26, accompanied by acetoxy ester 27.