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

‘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

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.

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.

Palladium-Catalyzed Csp3–H Bond mono-Aroyloxylation of O-Alkyl Substituted 2,4,6-Trimethoxybenzaldoxime Ethers

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1249-1255
Author(s):  
Wen-Li Qiao ◽  
Ling-Yan Shao ◽  
Ya-Hua Hu ◽  
Li-Hao Xing ◽  
Ke-Zuan Deng ◽  
...  
Keyword(s):  
Aromatic Ring ◽  
Aliphatic Alcohol ◽  
Cross Coupling ◽  
Aliphatic Alcohols ◽  
Aromatic Acid ◽  
Rapid Access ◽  
Site Selectivity ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group

A palladium-catalyzed Csp3–H bond mono-aroyloxylation of O-alkyl substituted oxime ethers has been developed by using 2,4,6-trimethoxybenzaldoxime as an exo-type directing group with exclusive site-selectivity. With the wide range of masked aliphatic alcohol substrates and aromatic acid coupling partners, the protocol allows rapid access to various 2-alkyl substituted glycol derivatives in synthetically useful to good yields. The employed directing group is readily removed, accordingly affording valuable functionalized aliphatic alcohols. When the solvent from hybrid DCE/HFIP to CH3CN, non-directed oxidative cross-coupling is observed between the electron-rich aromatic ring of substrates and aromatic acid partners.

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.

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