Asymmetric, Stereodivergent Synthesis of (−)-Clusianone Utilizing a Biomimetic Cationic Cyclization
نویسندگان
چکیده
منابع مشابه
Synthesis of Cyclic Alkenyl Triflates by a Cationic Cyclization Reaction and its Application in Biomimetic Polycyclizations and Synthesis of Terpenes.
Cyclic alkenyl triflates are useful intermediates in organic synthesis usually synthesized from ketones through a reaction involving enolization and trapping with a triflating agent. This sequence suffers from some stereochemical drawbacks owing to the basic conditions required. Herein, we describe a new acid-mediated cationic cyclization reaction of enyne derivatives (or alkynols) to access cy...
متن کاملSynthesis of the pyoverdin chromophore by a biomimetic oxidative cyclization.
The fluorescent dihydropyrimido[1,2-a]quinoline chromophore of the pyoverdin siderophores has been synthesized by a biomimetic oxidative cyclization using an iodine(III) reagent, followed by elimination and dehydrogenation.
متن کاملAsymmetric syntheses of 8-oxabicyclo[3,2,1]octanes: a cationic cascade cyclization.
tropane alkaloids, and consequently there is an increasing interest in their potential pharmaceutical use, particularly against cocaine abuse. Compelled by the interesting biological activities of 8oxatropanes, many groups have embarked on the search for new methodologies to construct this bicyclic structure. For example, Molander and co-workers have reported a Lewis acid promoted double allyla...
متن کاملThe enantioselective total synthesis of (+)-clusianone.
(+)-Clusianone, an exo-type B PPAP with reported anti-HIV and chemoprotective activities, was synthesized in eleven steps with 97% ee starting from acetylacetone. An enantioselective decarboxylative Tsuji-Trost-allylation and a Ru-catalyzed ring-closing metathesis-decarboxylative allylation were used to control both diastereo- and enantioselectivity.
متن کاملCatalytic asymmetric [3 + 2]-cycloaddition for stereodivergent synthesis of chiral indolyl-pyrrolidines.
The stereochemical divergent synthesis of indolyl-pyrrolidines was accomplished using an imidazoline-aminophenol (IAP)-Ni(OAc)2 complex and a bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 complex. The former catalyzed exo'-selective asymmetric [3 + 2] cyclization of iminoesters with indolyl nitroalkenes, and the latter catalyzed the reaction in an endo-selective manner. These catalysts are tol...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Angewandte Chemie International Edition
سال: 2014
ISSN: 1433-7851
DOI: 10.1002/anie.201404437