132969-62-1Relevant 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.
Expeditious synthesis of a key C9-C21 subunit of the aplysiatoxins and oscillatoxins
Walkup,Kane,Boatman Jr.,Cunningham
, p. 7587 - 7590 (2007/10/02)
The C9-C21 portion of the aplysiatoxin/oscillatoxin bluegreen algal metabolites was synthesized as the 9-aldehyde bearing a tert-butyldimethylsilyl ether group on the C11 hydroxyl and a trimethylsilylethoxymethyl ether gro