Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes.

نویسندگان

  • Ian B Spurr
  • Richard C D Brown
چکیده

The synthesis of the subgroups of acetogenins containing non-adjacent bis-THF and non-adjacent THF-THP core units is reviewed. Specifically, total syntheses of gigantecin, 4-deoxygigantecin, cis-sylvaticin, squamostatin-C, squamostatin-D, sylvaticin and mucocin are discussed.

برای دانلود رایگان 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

Inhibitory activities of three annonaceous acetogenins on NADH oxidase of chicken liver mitochondria.

Annonaceous acetogenins (ACG) are natural products found in the plant family Annonaceae and which strongly inhibited mitochondrial complex I. The inhibition of NADH oxidase of chicken liver mitochondria by three different structural ACG was studied here, and ACG was shown to have potent inhibitory activities similar to rotenone for NADH oxidase. The IC(50) values indicated that bis-adjacent tet...

متن کامل

Four mono-tetrahydrofuran ring acetogenins, montanacins B-E, from Annona montana.

Four novel mono-tetrahydrofuran (THF) acetogenins, montanacins B-E (1-4), were isolated from the ethanolic extract of the leaves of Annona montana. The structures of 1-4 were established by spectroscopic methods and their absolute stereochemistries were determined by the advanced Mosher ester method. Montancins D (3) and E (4) bear a non-adjacent tetrahydropyran (THP) ring along with a THF ring...

متن کامل

Quinone-annonaceous acetogenins: synthesis and complex I inhibition studies of a new class of natural product hybrids.

The natural product hybrids quinone-mucocin and quinone- squamocin D were synthesized. In these hybrids, the butenolide unit of the annonaceous acetogenins mucocin and squamocin D is exchanged for the quinone moiety of the natural complex I substrate ubiquinone. For both syntheses, a modular, highly convergent approach was applied. Quinone-mucocin was constructed out of a tetrahydropyran (THP) ...

متن کامل

Asymmetric synthesis of bis-tetrahydrofuran cores in annonaceous acetogenins.

The bis-THF cores of annonaceous acetogenins were synthesized using (3R,4R)-1,5-hexadiene-3,4-diol (1) as the sole source of carbon atoms. The methylene acetal function was applied as a new linker/tether to facilitate the ring-closing metathesis.

متن کامل

Synthesis of annonacin isolated from Annona densicoma.

A total synthesis of annonacin (1) was accomplished by using versatile chiral building block 2 for synthesizing the mono-tetrahydrofuran (THF) annonaceous acetogenins.

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

عنوان ژورنال:
  • Molecules

دوره 15 1  شماره 

صفحات  -

تاریخ انتشار 2010