Macrocyclization by nickel-catalyzed, ester-promoted, epoxide-alkyne reductive coupling: total synthesis of (-)-gloeosporone.
نویسندگان
چکیده
Ringing the changes: The total synthesis of the title compound centers around a novel strategy that employs a nickel(0)-phosphine complex and triethyl borane in an efficient closure of a 14-membered ring through C--C bond formation (see scheme; cod=cyclooctadiene). The synthesis was accomplished in 10 steps and in approximately 9 % overall yield.
منابع مشابه
Strategic use of nickel(0)-catalyzed enyne-epoxide reductive coupling towards the synthesis of (-)-cyatha-3,12-diene.
Various situations are explored in which the nickel(0)-catalyzed enyne-epoxide reductive coupling was utilized to access key intermediates towards the total synthesis of (-)-cyatha-3,12-diene (1). Enantioenriched 3,5-dien-1-ols with a variety of functionality were obtained in a straightforward manner from easily accessible 1,3-enynes and terminal epoxides.
متن کاملA reductive coupling strategy towards ripostatin A
Synthetic studies on the antibiotic natural product ripostatin A have been carried out with the aim to construct the C9-C10 bond by a nickel(0)-catalyzed coupling reaction of an enyne and an epoxide, followed by rearrangement of the resulting dienylcyclopropane intermediate to afford the skipped 1,4,7-triene. A cyclopropyl enyne fragment corresponding to C1-C9 has been synthesized in high yield...
متن کاملMethyltransferase-directed covalent coupling of fluorophores to DNA† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04229e Click here for additional data file.
We report an assay for determining the number of fluorophores conjugated to single plasmid DNA molecules and apply this to compare the efficiency of fluorophore coupling strategies for covalent DNA labelling. We compare a copper-catalyzed azide-alkyne cycloaddition reaction, amine to N-hydroxysuccinimidyl ester coupling reaction and strain-promoted azide-alkyne cycloaddition reaction for fluore...
متن کاملRegioselective nickel-catalyzed reductive couplings of enones and allenes.
Catalytic reductive coupling processes have been developed in numerous contexts as a strategy for the regioand stereoselective installation of alkenes. The direct coupling of a polar p system with a relatively nonpolar p system is often a successful strategy for selectively accomplishing synthetically desirable heterocouplings while avoiding undesired homocoupling of either reagent. For example...
متن کاملtrans‐Hydrogenation: Application to a Concise and Scalable Synthesis of Brefeldin A†
The important biochemical probe molecule brefeldin A (1) has served as an inspirational target in the past, but none of the many routes has actually delivered more than just a few milligrams of product, where documented. The approach described herein is clearly more efficient; it hinges upon the first implementation of ruthenium-catalyzed trans-hydrogenation in natural products total synthesis....
متن کاملذخیره 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 ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Angewandte Chemie
دوره 48 29 شماره
صفحات -
تاریخ انتشار 2009