252342-45-3Relevant articles and documents
Evolution of a gram-scale synthesis of (+)-discodermolide
Smith III, Amos B.,Beauchamp, Thomas J.,LaMarche, Matthew J.,Kaufman, Michael D.,Qiu, Yuping,Arimoto, Hirokazu,Jones, David R.,Kobayashi, Kaoru
, p. 8654 - 8664 (2007/10/03)
An efficient, highly convergent, stereocontrolled total synthesis of the potent antimitotic agent (+)-discodermolide (1) has been achieved on gram scale. Key elements of the successful strategy include (1) elaboration of three advanced fragments from a common precursor (CP) which embodies the repeating stereochemical triad of the discodermolide backbone, (2) σr-bond installation of the Z trisubstituted olefin, exploiting a modified Negishi cross-coupling reaction, (3) synthesis of a late-stage phosphonium salt utilizing high pressure, and (4) Wittig installation of the Z disubstituted olefin and the terminal (Z)-diene.