Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.

نویسندگان

  • Partha Ghosh
  • Yue Zhang
  • Thomas J Emge
  • Lawrence J Williams
چکیده

A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

The Syntheses and Characterization of Three Novel Macrocyclic Polyether Ligands and Some of Their Alkaline Metal Complexes

The macrocyclic ligands 2,3,5,6-Bis{3’-bromo-5’-tert-butyl benzo-5-phenyl benzo} 12C3 (L1), 2,3,5,6-bis{3’-bromo-5’-tert butyl-benzo-5’-phenyl-benzo}15C4 (L2), 2,3,5,6-bis{3’-bromo-5’-tert butyl-benzo-5’-phenyl-benzo}18C5 (L3) have been synthesized and their alkaline metal compounds with NaClO4∙H2O and KClO4  have ...

متن کامل

Synthesis of Macrolide Antibiotics. IV. Stereoselective Syntheses of the 3-0-Methyl and the 11-0-Methyl Derivatives of the C(1)-C(6) Segment of Erythrono1ides A and B and the C(9)-C(15) Segment of Erythronolide A, Respectively.tf

By appropriate dissection of the macrocyclic lactone ring of methymycin erythromycins A and B, picromycin and narbomycin, carbohydrate-like structural segments were obtained. The finding that the anomeric configuration of a glycopyranoside effectively controls the stereochemistry of various addition reactions to sp' (C=O and C=C) carbon atoms of a glycopranoside ring led to the development of a...

متن کامل

Synthesis, biological and molecular modeling studies of macrocyclic complexes of trivalent metal ions

The macrocyclic complexes of biological importance with power transition metals are synthesized by template methodology leading to the formation of the complex [MLX] X2; where L is macrocyclic ligand derived from 3,4-diaminotoluene, 2,4-thiazolidinedione, M=Cr (III) and Fe(III) X is Cl-, CH3COO- or NO3_.Characterisation of these complexes are through with the assistance of elemental analyses(CH...

متن کامل

Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems.

The stereoselective synthesis of a challenging macrocyclic polyene scaffold, containing a sensitive vinyl ether motif, has been accomplished using O,C-dilithiation/selective C-alkylation, Pd-catalysed etherification and Wittig reactions as key steps. An end-game macrocyclisation strategy employed a regio- and stereoselective Stille cross-coupling using Pd(Br)(N-Succ)(AsPh3)2 (AsCat) as the prec...

متن کامل

Binuclear Complex of Zinc and Copper with Unsymmetrical Macrocyclic Ligand as Sensitizer in Nanocrystaline TiO2 Solar Cells

Dye sensitized solar cells (DSSCs) are considered as one of the most promising alternativerenewable energy sources. In the structure of DSSCs, a photosensitizer composed of transitionmetal complexes is used to harvest light. In this work a binuclear complex containing twopropionitrile pendant arms [ZnLCu(OAC)]PF6 {L = 1, 6- bis (2-cyanoethyl) -2, 5-bis (2-hydroxy3-formyl-5-methylbenzyl)-2, 5- d...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic letters

دوره 11 19  شماره 

صفحات  -

تاریخ انتشار 2009