Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group.
نویسندگان
چکیده
A concise total synthesis of the plant alkaloid (±)-leuconolam (1) has been achieved. A regio- and diastereoselective Lewis-acid mediated allylative cyclization was used to establish, simultaneously, two adjacent tetrasubstituted carbon centers. Furthermore, an essential arene cross-coupling to a hindered haloalkene was enabled by the use of a novel 2-anilinostannane.
منابع مشابه
Enantioselective total synthesis of marine diterpenoid clavulactone.
The key steps in the synthesis of clavulactone are formation of an enantiopure cyclopentane precursor by epoxide rearrangement and intramolecular carbonyl-ene reaction, construction of the 3,4-dihydro-2H-pyran ring by intermolecular hetero-Diels-Alder reaction, closure of the eleven-membered ring, and finally generation of the lactone functionality by chemoselective allylic C(sp(3))-H oxidation.
متن کاملSynthesis of oxygen-containing heterocyclic compounds based on the intramolecular O–H insertion and Wolff rearrangement of a-diazocarbonyl compounds
The addition products of Ti(IV)-enolate derived from b-keto a-diazo carbonyl compound to ketones or a,b-unsaturated compounds were subjected to Rh2(OAc)4-catalyzed and photo-induced diazo decomposition. The Rh2(OAc)4-catalyzed reaction afforded intramolecular O–H insertion products, while the photo-induced reaction gave Wolff rearrangement/intramolecular nucleophilic addition products. The tran...
متن کاملPalladium-Catalyzed Decarbonylative Dehydration for the Synthesis of α-Vinyl Carbonyl Compounds and Total Synthesis of (-)-Aspewentins A, B, and C.
The direct α-vinylation of carbonyl compounds to form a quaternary stereocenter is a challenging transformation. It was discovered that δ-oxocarboxylic acids can serve as masked vinyl compounds and be unveiled by palladium-catalyzed decarbonylative dehydration. The carboxylic acids are readily available through enantioselective acrylate addition or asymmetric allylic alkylation. A variety of α-...
متن کاملSynthesis and Characterization of Polyamide Containing Maleimide Pendant Group
A series of new polyamides containing maleimide pendant group were prepared by low temperature polycondensation of 5-(4-(2,5-dioxo-2H-pyrrol-1(5H)-yl)benzamido)isophthaloyl chloride as a new monomer with various aromatic diamines in NMP. Monomer and polymers structures were identified through FT-IR, 1H-NMR and elemental analysis. Obtained polymers were soluble in polar solvents and non solu...
متن کاملIntramolecular carbonyl carbonyl interactions in W, Mo and Fe complexes containing the g-N-maleimidato ligand: X-ray, DFT and AIM studies
The crystal structures of (g-C5H5)W(CO)3(g -N-maleimidato) and (g-C5H5)Fe(CO)2(g -N-maleimidato) complexes were determined by single crystal X-ray diffraction. The molecular geometries of both structures are compared with those of the Mo analog of the W complex and ethyl-N-maleimide in order to find a relation between the geometrical features and the rate constants of the addition reaction of t...
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:
- Chemical science
دوره 4 5 شماره
صفحات -
تاریخ انتشار 2013