Total synthesis of (+)-amphidinolide A. Structure elucidation and completion of the synthesis

BM Trost, PE Harrington, JD Chisholm…

Index: Trost, Barry M.; Wrobleski, Stephen T.; Chisholm, John D.; Harrington, Paul E.; Jung, Michael Journal of the American Chemical Society, 2005 , vol. 127, # 39 p. 13589 - 13597

Full Text: HTML

Citation Number: 40

Abstract

The structure elucidation of (+)-amphidinolide A, a cytotoxic macrolide, has been accomplished by employing a combination of NMR chemical shift analysis and total synthesis. The 20-membered ring of amphidinolide A was formed by a ruthenium-catalyzed alkene-alkyne coupling to forge the C15-C16 bond. Using the reported structure 1 as a starting point, a number of diastereomers of amphidinolide A were prepared. Deviations of ...

Related Articles:

The Asymmetric Aza??Claisen Rearrangement: Development of Widely Applicable Pentaphenylferrocenyl Palladacycle Catalysts

[Fischer, Daniel F.; Barakat, Assem; Xin, Zhuo-Qun; Weiss, Matthias E.; Peters, Rene Chemistry - A European Journal, 2009 , vol. 15, # 35 p. 8722 - 8741]

Phosphonium salts and phosphoranes. Part 5. Thermal and electron-impact induced fragmentation of heteroaroylmethylenetriphenylphosphoranes.

[Brittain, Judith M.; Jones, R. Alan; Taheri, Sayed Ali Naghi Tetrahedron, 1992 , vol. 48, # 36 p. 7609 - 7618]

Palladium-mediated cross-coupling reactions involving 3-substituted alkyl (E)-2, 3-dibromopropenoates and arylzinc or aryltin derivatives

[Rossi, Renzo; Bellina, Fabio; Carpita, Adriano; Mazzarella, Felice Tetrahedron, 1996 , vol. 52, # 11 p. 4095 - 4110]

1, 2, 3-Selenadiazole and its derivatives

[Lalezari,I. et al. Journal of Organic Chemistry, 1971 , vol. 36, p. 2836 - 2838]

Reaction of 1, 2, 3-Selenadiazoles with Phosphines

[Arsenyan; Oberte; Rubina; Belyakov; Lukevics Chemistry of Heterocyclic Compounds, 2004 , vol. 40, # 4 p. 503 - 506]

More Articles...