Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
نویسندگان
چکیده
Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three-component allylboration-Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (-)-clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation-borylation reaction to attach the cyclopropyl-containing side chain.
منابع مشابه
Urea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation- condensation Tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols
An efficient one-pot oxidation/condensation tandem process has been developed for the synthesis of 2-substituted benzimidazole derivatives from benzylic alcohols and 1,2-phenylenediamine with use of urea-hydrogen peroxide/silica phosphoric acid as a bifunctional catalyst. This method provides a rapid and efficient access to 2-substituted benzimidazoles.
متن کاملUrea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation- condensation Tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols
An efficient one-pot oxidation/condensation tandem process has been developed for the synthesis of 2-substituted benzimidazole derivatives from benzylic alcohols and 1,2-phenylenediamine with use of urea-hydrogen peroxide/silica phosphoric acid as a bifunctional catalyst. This method provides a rapid and efficient access to 2-substituted benzimidazoles.
متن کاملDiastereoselective synthesis of 2,3,6-trisubstituted tetrahydropyran-4-ones via Prins cyclizations of enecarbamates: a formal synthesis of (+)-ratjadone A.
Enecarbamates are shown to be excellent terminating groups for Prins cyclizations. A noteworthy feature of this methodology is the easy, stereoselective construction of the cyclization precursors by alkylation of metalated (E)-enecarbamates with epoxides. The stereochemistry of the resultant trisubstituted (E)-enecarbamates is then transferred with high fidelity to afford the frequently observe...
متن کاملApplication of Green Procedure for the Synthesis of Substituted Pyrroles: Multi-component Reaction of Oxalyl Chloride
A novel, convenient and efficient approach to synthesis of pyrrole derivatives via the reaction of primary amines, alkyl propiolates and oxalyl chloride is described. The method offers several advantages including high yields of products and performing reaction in water as the solvent.
متن کاملA Clean and Highly Efficient Synthesis of Oxindole Substituted Pyrrolo[2,3-d]Pyrimidines under Ultrasound Irradiation
A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. All reactions performed effic...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
دوره 55 شماره
صفحات -
تاریخ انتشار 2016