327603-45-2Relevant articles and documents
Apoptolidin A: Total synthesis and partially glycosylated analogues
Wehlan, Hermut,Dauber, Mario,Fernaud, M. Teresa Mujica,Schuppan, Julia,Keiper, Sonja,Mahrwald, Rainer,Garcia, M.-Elisa Juarez,Koert, Ulrich
, p. 7378 - 7397 (2007/10/03)
The total synthesis of apoptolidin A is described employing an early glycosylation strategy. Strategic disconnections were chosen between C11-C12 (cross-coupling) and C19O-C1 (macrocyclization). The cis-selective glycosylation at C9-OH was achieved with the new SIBA protective group at O2/O3 of the L-glucose residue. Auxiliary substitutents at the 2-position of the 2-deoxy sugars were applied to form selectively the glycosidic linkages of the C27 disaccharide. The cross-coupling of the glycosylated northern half with the glycosylated southern half was achieved with Cu1-thiophene carboxylate. The macrocyclization of a trihydroxy carboxylic acid produced the 20-membered macrolide selectively. H2SiF6 was suitable for the final deprotection of the silyl ethers and the conversion of the C21 methylketal into the hemiketal. The synthetic flexibility of the approach was proven by the synthesis of some glycovariants.
Total synthesis of apoptolidin
Wehlan, Hermut,Dauber, Mario,Fernaud, M.-Teresa Mujica,Schuppan, Julia,Mahrwald, Rainer,Ziemer, Burkhard,Garcia, M.-Elisa Juarez,Koert, Ulrich
, p. 4597 - 4601 (2007/10/03)
A ring-size-selective macrolactonization and the early introduction of the saccharide portions are the main features of a total synthesis of the 20-membered macrolide apoptolidin (see formula), which induces apoptosis in rat glia cells transformed with oncogenes.
Total Synthesis of Apoptolidin: Construction of Enantiomerically Pure Fragments
Nicolaou,Fylaktakidou, Konstantina C.,Monenschein, Holger,Li, Yiwei,Weyershausen, Bernd,Mitchell, Helen J.,Wei, Heng-Xu,Guntupalli, Prasuna,Hepworth, David,Sugita, Kazuyuki
, p. 15433 - 15442 (2007/10/03)
A general strategy for the total synthesis of the antitumor agent apoptolidin (1) is proposed, and the chemical synthesis of the defined key building blocks (4, 5, 6, 8, and 9) in their enantiomerically pure forms is described. The projected total synthes
Synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 12
Varga, Zsolt,Bajza, István,Batta, Gyula,Lipták, András
, p. 3145 - 3148 (2007/10/03)
An effective synthesis of the pentasaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serovar 12 in the protected p-nitrophenyl glycoside, using a 3+2 block synthesis strategy, is described.
Total synthesis of apoptolidin: Part 1. Retrosynthetic analysis and construction of building blocks
Nicolaou,Li, Yiwei,Fylaktakidou, Konstantina C.,Mitchell, Helen J.,Wei, Heng-Xu,Weyershausen, Bernd
, p. 3849 - 3854 (2007/10/03)
No less than 30 stereogenic elements, a highly unsaturated 20-membered macrocyclic system, four carbohydrate units, and unique biological activity, make the natural occurring apoptolidin (1) a challenging synthetic target. The retrosynthetic analysis reve