Toward the total synthesis of goniodomin A, an actin-targeting marine polyether macrolide: convergent synthesis of the C15-C36 segment.

نویسندگان

  • Tomoyuki Saito
  • Haruhiko Fuwa
  • Makoto Sasaki
چکیده

Stereoselective convergent synthesis of the C15-C36 segment of goniodomin A, an actin-targeting marine polyether macrolide natural product, has been achieved. The present synthesis features palladium(0)-catalyzed, copper(I)-mediated Liebeskind-Srogl cross-coupling as the fragment assembly process.

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

Assignment of the absolute configuration of goniodomin A by NMR spectroscopy and synthesis of model compounds.

The complete absolute configuration of goniodomin A, an actin-targeting polyether macrolide isolated from the marine dinoflagellate Alexandrium hiranoi, was established from analysis of ROESY experiments and coupling constants, synthesis of suitable model compounds for NMR spectroscopic comparisons, degradation experiments, and correlation with synthetic reference compounds.

متن کامل

Total Synthesis of the Antimitotic Marine Macrolide (−)-Leiodermatolide**

Leiodermatolide is an antimitotic macrolide isolated from the marine sponge Leiodermatium sp. whose potentially novel tubulin-targeting mechanism of action makes it an exciting lead for anticancer drug discovery. In pursuit of a sustainable supply, we report a highly stereocontrolled total synthesis (3.2% yield) based on a convergent sequence of palladium-mediated fragment assembly and macrolac...

متن کامل

Total synthesis of a stereoisomer of bistramide C and assignment of configuration of the natural product.

After the isolation of the bioactive polyether bistramide C from the marine ascidian Lissoclinum bistratum in 1988, NMR spectroscopic investigations over the next 12 years reduced the total number of possible stereoisomers of this compound from 1024 to 32. Based on the preparation of segments of the natural product as well as the total synthesis of a randomly selected stereoisomer of bistramide...

متن کامل

Synthesis and Characterization of New Macrocyclic Polyether-Diester Ligands Containing A 4H-Pyran-4-One Subcyclic Unit

New macrocyclic polyether-diester ligands (3-5) containing the 4H-pyran-4-one subcyclic unit have been prepared by treating various glycols with dimethyl chelidonate (10). In the reaction of compound 10 with ethylene glycol and diethylene glycol, two noncyclic diester and tetraester (6-9) were produced in each case. The new marcocyclic ligand 4 formed stable complexes with benzylammonium pe...

متن کامل

Stereocontrolled and convergent total synthesis of amphidinolide T3.

Stereocontrolled and convergent total synthesis of amphidinolide T3 has been described. A retrosynthetic scheme was constructed that led to the recognition of readily available and enantiomerically related compounds as starting materials for the total synthesis of amphidinolide T3. Thus, the two key building blocks 6 and 7 were defined as subtargets and synthesized in optically active forms. Th...

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 22  شماره 

صفحات  -

تاریخ انتشار 2009