A stereoselective, Sm(II)-mediated approach to decorated cis-hydrindanes: synthetic studies on faurinone and pleuromutilin.

نویسندگان

  • Thomas J K Findley
  • David Sucunza
  • Laura C Miller
  • Matthew D Helm
  • Madeleine Helliwell
  • David T Davies
  • David J Procter
چکیده

The cis-hydrindane motif is found in a number of natural products that display important biological activity. A flexible, stereoselective approach to the framework has been developed that features highly diastereoselective, SmI(2)-mediated cyclisations. The strategy has been exploited in the first synthesis of the proposed structure of faurinone and an approach to the skeleton of the antibacterial natural product, pleuromutilin.

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

Copper‐Catalyzed Double Additions and Radical Cyclization Cascades in the Re‐Engineering of the Antibacterial Pleuromutilin

A general synthetic sequence involving simply prepared starting materials provides rapid access to diverse, novel tricyclic architectures inspired by pleuromutilin. Sm(II) -mediated radical cyclization cascades of dialdehydes, prepared using a new, one-pot, copper-catalyzed double organomagnesium addition to β-chlorocyclohexenone, proceed with complete sequence selectivity and typically with hi...

متن کامل

The Effect of System-Nested, Genre-Oriented, Structurally-Mediated Model (SGSM) of Writing Instruction, and Swalesian Model (SM) upon Iranian Learners’ Writing Performance: A Comparative Study

The purpose of the present study was first to offer a tentative solution to the problems observed in writing pedagogy in Iran by devising a more comprehensive approach to genre-based writing instruction. In the second phase, a quasi-experimental research design was adopted to determine how effective the model was in writing instruction, compared with the traditional, product-oriented approach, ...

متن کامل

Stereoselective Permeation of Tretinoin and Isotretinoin through Enhancer-Treated Rat Skin. II. Effects of Lipophilic Penetration Enhnacers

Many properties of chemicals depend on their stereochemistry. Among these, the effects of stereoisomerism on percutaneous absorption of drugs are not well studied. We have previously shown that permeation of tretinoin and isotretinoin (two geometric isomers) through hydrophilic enhancers-treated rat skin is stereoselective. As, depending on their lipophilicity, penetration enhancers can change ...

متن کامل

Stereoselective Permeation of Tretinoin and Isotretinoin through Enhancer-Treated Rat Skin. II. Effects of Lipophilic Penetration Enhnacers

Many properties of chemicals depend on their stereochemistry. Among these, the effects of stereoisomerism on percutaneous absorption of drugs are not well studied. We have previously shown that permeation of tretinoin and isotretinoin (two geometric isomers) through hydrophilic enhancers-treated rat skin is stereoselective. As, depending on their lipophilicity, penetration enhancers can change ...

متن کامل

Synthesis of bridged oxafenestranes from pleuromutilin.

Fenestranes are an intriguing class of highly strained molecules possessing a quaternary carbon with bonds that deviate from the canonical tetrahedral geometry. Herein we report the discovery that the natural product pleuromutilin can be used as a structurally complex starting material for the synthesis of a series of bridged cis,cis,cis,cis-[4.5.5.5]- and cis,cis,cis,cis-[4.5.7.5]oxafenestrane...

متن کامل

ذخیره در منابع من

ذخیره در منابع من قبلا به منابع من ذحیره شده

{@ msg_add @}


  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 & biomolecular chemistry

دوره 9 7  شماره 

صفحات  -

تاریخ انتشار 2011