scholarly journals Chiral cyclopentadienyl RhIII-catalyzed enantioselective cyclopropanation of electron-deficient olefins enable rapid access to UPF-648 and oxylipin natural products

2019 ◽  
Vol 10 (9) ◽  
pp. 2773-2777 ◽  
Author(s):  
Coralie Duchemin ◽  
Nicolai Cramer
Keyword(s):  
Natural Products ◽  
Rapid Access

Chiral cyclopentadienyl-RhIII complexes catalyze enantioselective cyclopropanations of electron-deficient olefins with N-enoxysuccinimides and are used for syntheses of oxylipins and UPF-648.

ChemInform Abstract: “Aromatic Ring Umpolung”, a Rapid Access to the Main Core of Several Natural Products.

ChemInform ◽  
2010 ◽  
Vol 41 (45) ◽  
pp. no-no
Author(s):  
Kimiaka C. Guerard ◽  
Cyrille Sabot ◽  
Marc-Andre Beaulieu ◽  
Marc-Andre Giroux ◽  
Sylvain Canesi
Keyword(s):  
Natural Products ◽  
Aromatic Ring ◽  
Rapid Access

scholarly journals Synthesis of substituted tetrahydroisoquinolines by lithiation then electrophilic quench

2016 ◽  
Vol 14 (21) ◽  
pp. 4908-4917 ◽  
Author(s):  
Ruaa A. Talk ◽  
Alexia Duperray ◽  
Xiabing Li ◽  
Iain Coldham
Keyword(s):  
Natural Products ◽  
Rapid Access

Lithiation then electrophilic quench of tetrahydroisoquinolines provides access to 1-substituted products. Removal of the N-Boc group allows rapid access to natural products such as (±)-crispine A.

scholarly journals A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products

2019 ◽  
Vol 10 (41) ◽  
pp. 9586-9590 ◽  
Author(s):  
Hai Huang ◽  
Wen Yang ◽  
Zuliang Chen ◽  
Zengwei Lai ◽  
Jianwei Sun
Keyword(s):  
Natural Products ◽  
Ring Opening ◽  
Catalytic Synthesis ◽  
Rapid Access ◽  
Oxetane Ring

A new catalytic protocol for the expedient synthesis of oxazolines from oxetanes is developed.

scholarly journals Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G

2016 ◽  
Vol 12 ◽  
pp. 2689-2693 ◽  
Author(s):  
Youngeun Jung ◽  
Dileep Kumar Singh ◽  
Ikyon Kim
Keyword(s):  
Natural Products ◽  
Suzuki Coupling ◽  
Synthetic Approach ◽  
Sonogashira Coupling ◽  
Cyclization Reactions ◽  
Aryl Ring ◽  
Rapid Access ◽  
Alkoxy Groups

The recognition of the local symmetric image within benzofuran-based natural oligostilbenoids guided us to design a modular synthetic approach to these molecules by utilizing a three-step sequence consisting of Sonogashira coupling, iodocyclization, and Suzuki coupling. During our synthesis, the relative reactivities of ester, aldehyde, and alkoxy groups on the same aryl ring toward the neighboring alkyne in the iodine-mediated cyclization reactions were explored. Starting from the symmetrical 3,5-dimethoxybenzyl alcohol, this route allowed rapid access to 2,3-diarylbenzofuran, a key intermediate to several oligostilbenoid natural products, in good overall yields.

‘Aromatic ring umpolung’, a rapid access to the main core of several natural products

Tetrahedron ◽  
2010 ◽  
Vol 66 (31) ◽  
pp. 5893-5901 ◽  
Author(s):  
Kimiaka C. Guérard ◽  
Cyrille Sabot ◽  
Marc-André Beaulieu ◽  
Marc-André Giroux ◽  
Sylvain Canesi
Keyword(s):  
Natural Products ◽  
Aromatic Ring ◽  
Rapid Access

A Free-Radical and Protecting-Group-Free Approach to (–)-Boschnialactone and γ-Lycorane

Synthesis ◽  
2019 ◽  
Vol 51 (10) ◽  
pp. 2207-2213 ◽  
Author(s):  
Alberto Basante-Avendaño ◽  
Víctor Guerra-Ayala ◽  
Alma Sánchez-Eleuterio ◽  
Alejandro Cordero-Vargas
Keyword(s):  
Natural Products ◽  
Free Radical ◽  
Protecting Group ◽  
Dicarbonyl Compound ◽  
Rapid Access

The protecting-group-free (PGF) and free-radical-based synthesis of two structurally different natural products, (–)-boschnialactone and γ-lycorane, is reported. The key step in both syntheses is a radical–ionic sequence for construction of the principal structure (a six-membered lactone and a 1,4-dicarbonyl compound, respectively), allowing short and rapid access to these natural products through a PGF route.

scholarly journals Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4143
Author(s):  
Tamie Suzuki ◽  
Nilamber A. Mate ◽  
Arijit A. Adhikari ◽  
John D. Chisholm
Keyword(s):  
Natural Products ◽  
Transition Metal ◽  
Small Molecule ◽  
Lewis Acid ◽  
Medicinal Chemistry ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Rapid Access ◽  
Privileged Scaffolds

2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

scholarly journals Stereoselective chromium- and molybdenum-mediated transformations of arenes

2004 ◽  
Vol 76 (3) ◽  
pp. 689-695 ◽  
Author(s):  
E. P. Kündig ◽  
Rita Cannas ◽  
C.-H. Fabritius ◽  
Gabriele Grossheimann ◽  
Mikhail Kondratenko ◽  
...  
Keyword(s):  
Natural Products ◽  
Metal Complexes ◽  
Final Section ◽  
Claisen Rearrangement ◽  
Arene Complexes ◽  
Asymmetric Syntheses ◽  
Rapid Access ◽  
Arene Complex ◽  
Key Steps ◽  
First Time

Tricarbonylchromium-mediated dearomatization provides a rapid access to substituted cyclohexadienes. Efficient asymmetric routes to planar chiral arene complexes and to substituted cyclohexadienes have been developed. The article sums up the main features of this chemistry. Highly enantiomerically enriched ortho-substituted benzaldehyde complexes are accessible via asymmetric lithiation followed by trapping with electrophiles. In different solvents, the trimethylsilyl complex exhibits [alpha] values ranging from −174 to +108 for the same enantiomer. Details of two asymmetric syntheses of natural products are given: the alkaloid lasubine I starting from a highly enantiomerically enriched planar chiral arene complex and the marine furanosesquiterpene acetoxytubipofuran. The latter is assembled via asymmetric dearomatization of a benzaldehyde imine complex. Other key steps include an Eschenmoser–Claisen rearrangement and a regio- and diastereoselective Pd-catalyzed allylic substitution. The final section deals with labile arene metal complexes. For the first time, dearomatization reactions mediated by the Mo(CO)3 group have been realized. The reactions show strong analogies to the Cr(CO)3-mediated reactions, but exhibit also marked differences: the arene–Mo bond is stronger, but more labile, and the sequential double additions show different selectivities compared to the chromium analogs.

scholarly journals Total synthesis of biseokeaniamides A–C and late-stage electrochemically-enabled peptide analogue synthesis

2020 ◽  
Vol 11 (39) ◽  
pp. 10752-10758 ◽  
Author(s):  
Yutong Lin ◽  
Lara R. Malins
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Late Stage ◽  
Peptide Analogue ◽  
Rapid Access ◽  
Structural Analogues

A late-stage electrochemical decarboxylation enables rapid access to structural analogues of biseokeaniamides A–C, cytotoxic lipopeptide natural products.

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