Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

نویسندگان

  • Andivelu Ilangovan
  • Shanmugasundar Saravanakumar
چکیده

A unified strategy was followed for the synthesis of three putrescine bisamides, (+)-grandiamide D, dasyclamide and gigantamide A, isolated from leaves of Aglaia gigantea, by making use of a common synthetic intermediate prepared by the Baylis-Hillman reaction. Asymmetric synthesis of the natural (+)-grandiamide D was accomplished from camphor sultam.

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

Et3N/H2O: A green and inexpensive organocatalytic medium for efficient Baylis-Hillman reaction

A new organocatalyzed method is developed for Baylis–Hillman reactions of cyclohex-2-enone with various aromatic aldehydes in the presence of water and catalytic quantities of triethylamine. All reactions take place at room temperature and relatively good yields of various products are obtained within a time frame which does not exceed 24 hours. The mild reaction conditions used in the present ...

متن کامل

Et3N/H2O: A green and inexpensive organocatalytic medium for efficient Baylis-Hillman reaction

A new organocatalyzed method is developed for Baylis–Hillman reactions of cyclohex-2-enone with various aromatic aldehydes in the presence of water and catalytic quantities of triethylamine. All reactions take place at room temperature and relatively good yields of various products are obtained within a time frame which does not exceed 24 hours. The mild reaction conditions used in the present ...

متن کامل

Microwave-Assisted Convenient Syntheses of 2-Indolizine Derivatives from Morita-Baylis-Hillman Adducts: New in silico Potential Ion Channel Modulators

Neste artigo, um estudo sintético assistido por irradiação de micro-ondas para produzir 2-indolizina-carbonitrila e 2-indolizina-carboxilato de metila em bons a altos rendimentos (70 e 81%) em uma etapa a partir de adutos de Morita-Baylis-Hillman (AMBH) é apresentado. Estes compostos foram subsequentemente transformados em altos rendimentos (94-100%) em três derivados 2-indolizínicos. Os cinco ...

متن کامل

Synthesis, Molecular Docking Studies and Antibacterial Evaluation of Baylis-Hillman Adducts of Coumarin and Pyran Derivatives Using Ionic Liquid under Microwave Irradiation

The Baylis-Hillman adducts 3(a-e) and 6(a-g) were prepared by the reaction of appropriate aldehydes with alkenes in presence of catalytic amount of urotropine with ionic liquids under microwave irradiation. Structures of the newly synthesized compounds were characterized by spectral studies. The antibacterial studies of Baylis-Hilmann compounds for analysis of the structural requirements for an...

متن کامل

Different Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate

In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausib...

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:

دوره 10  شماره 

صفحات  -

تاریخ انتشار 2014