Synthesis of the C(1)–C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C–C Bond Formation
نویسندگان
چکیده
The C(1)-C(13) fragment of the antimitotic marine macrolide leiodermatolide is prepared in seven steps via hydrogenative and transfer-hydrogenative reductive C-C couplings. A hydrogen-mediated reductive coupling of acetylene with a Roche-type aldehyde is used to construct C(7)-C(13). A 2-propanol-mediated reductive coupling of allyl acetate with (E)-2-methylbut-2-enal at a low loading of iridium (1 mol %) is used to construct C(1)-C(6), which is converted to an allylsilane using Oestereich's copper-catalyzed allylic substitution of Si-Zn reagents. The union of the C(1)-C(6) and C(7)-C(13) fragments is achieved via stereoselective Sakurai allylation.
منابع مشابه
Nano-Fe3O4 as a heterogeneous recyclable magnetically separable catalyst for synthesis of nitrogen fused imidazoheterocycles via double C-N bond formation
An efficient and convenient approach towards the synthesis of nitrogen fused imidazoheterocycles through double C-N bond formation in a single step has been achieved with a good range of substituted phenacyl bromides in the presence of magnetically recoverable Fe3O4 as a green heterogeneous nanocatalyst. The present approach was found to be environmentally benign and econo...
متن کاملNano-Fe3O4 as a heterogeneous recyclable magnetically separable catalyst for synthesis of nitrogen fused imidazoheterocycles via double C-N bond formation
An efficient and convenient approach towards the synthesis of nitrogen fused imidazoheterocycles through double C-N bond formation in a single step has been achieved with a good range of substituted phenacyl bromides in the presence of magnetically recoverable Fe3O4 as a green heterogeneous nanocatalyst. The present approach was found to be environmentally benign and econo...
متن کاملBaker’s yeast catalyzed Henry reaction: Biocatalytic C-C bond formation
The C-C bond formation is an important reaction in organic synthesis to obtain value-added intermediates. Therefore, in this paper an attempt has been made to accelerate the Henry reaction (C-C bond formation) between aryl aldehydes and nitromethane using less expensive whole cell biocatalyst, baker’s yeast (BY). The scope of the methodology was also tested for the heteryl aldehyde i.e. 2-chlor...
متن کاملBaker’s yeast catalyzed Henry reaction: Biocatalytic C-C bond formation
The C-C bond formation is an important reaction in organic synthesis to obtain value-added intermediates. Therefore, in this paper an attempt has been made to accelerate the Henry reaction (C-C bond formation) between aryl aldehydes and nitromethane using less expensive whole cell biocatalyst, baker’s yeast (BY). The scope of the methodology was also tested for the heteryl aldehyde i.e. 2-chlor...
متن کاملPlatinum-oxygen Bond Formation: Kinetic and Mechanistic Studies
Reaction of [PtMe(C^N)(SMe2)] (C^N = 2-phenylpyridinate (ppy); 1a, C^N = benzo[h]quinolate, (bhq); 1b) with hydrogen peroxide gives the platinum(IV) complexes trans-[PtMe(OH)2(C^N)(H2O)] (C^N = ppy; 3a, C^N = bhq, 3b) bearing platinum-oxygen bonds. The Pt(II) complexes 1a and 1b have 5dπ(Pt)→π*(C^N) MLCT band in the visible region which is used to easily follow the kinetic of its reaction with ...
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 19 شماره
صفحات -
تاریخ انتشار 2017