Sarinfacetamides A and B, Nitrogenous Diterpenoids with Tricyclo[6.3.1.01,5]dodecane Scaffold from the South China Sea Soft Coral Sarcophyton infundibuliforme

10.1021/acs.orglett.8b00842

2018-04-11

Two novel nitrogenous diterpenoids, sarinfacetamides A (1) and B (2), featuring an uncommon tricyclo[6.3.1.01,5]dodecane scaffold, and a known related diterpene (3) were isolated from the South China Sea soft coral Sarcophyton infundibuliforme. Their structur...

Studies toward the Synthesis of Iriomoteolide-2a: Construction of the C(6)–C(28) Fragment

10.1021/acs.orglett.8b00542

2018-04-10

The synthesis of an appropriately functionalized advanced C(6–28) fragment (3) of the marine macrolide iriomoteolide-2a (1) has been achieved in a highly efficient manner. The C(6)–C(18) fragment of 1 is prepared via a radical cyclization of a vinyl ether int...

Aroyl Isocyanates as 1,4-Dipoles in a Formal [4 + 1]-Cycloaddition Approach toward Oxazolone Construction

10.1021/acs.orglett.8b00656

2018-04-10

A formal phosphine-mediated [4 + 1]-cycloaddition between a 1,2-dicarbonyl and an aroyl isocyanate to provide oxazolones bearing a disubstituted C5 center is described. By exploiting the carbene-like reactivity of oxyphosphonium enolates as C1 synthons and ar...

Controlled Synthesis of C70 Equatorial Multiadducts with Mixed Addends from an Equatorial Diadduct: Evidence for an Electrophilic Carbanion

10.1021/acs.orglett.8b00672

2018-04-10

Controlled synthesis of the equatorial tetra-, hexa-, and octaorgano[70]fullerenes with mixed addends was achieved via the reaction of equatorial 7,23-Bn2C70 with MeO– and ArCH2Br. The products were structurally characterized by single crystal X-ray diffracti...

Nitrate-promoted Selective C–H Fluorination of Benzamides and Benzeneacetamides

10.1021/acs.orglett.8b00793

2018-04-10

A versatile and site-selective nitrate-promoted C–H bond fluorination using various weak coordinating amides as intrinsic directing groups was developed. Diverse tertiary and secondary amides underwent selective aromatic C–H bond fluorination, which features ...

Direct ortho-Selective C–H Functionalization of Carboxybenzyl-Protected Arylalkylamines via Ir(III)-Catalyzed C–H Activation

10.1021/acs.orglett.8b00797

2018-04-10

A convenient and practical approach to synthesize ortho-alkynylated arylalkylamines through ortho-selective C–H functionalization has been developed using Cbz-amide as the directing group and Ir(III) as the catalyst. Various substrates were well tolerated, af...

Schincalactones A and B, Two 5/5/6/11/3 Fused Schinortriterpenoids with a 13-Membered Carbon Ring System from Schisandra incarnata

10.1021/acs.orglett.8b00889

2018-04-10

Two novel schinortriterpenoids (SNTs), schincalactones A (1) and B (2), featuring a unique 5/5/6/11/3 ring system, together with schincalide B (3), were isolated from Schisandra incarnata. Their structures were elucidated by detailed spectroscopic analysis, a...

Direct Synthesis of 2-Methylbenzofurans from Calcium Carbide and Salicylaldehyde p-Tosylhydrazones

10.1021/acs.orglett.8b00676

2018-04-10

A new methodology for the construction of methyl-substituted benzofuran rings from the reactions of calcium carbide with salicylaldehyde p-tosylhydrazones/2-hydroxyacetophenone p-tosylhydrazones is described. Various 2-methylbenzofurans and 2,3-dimethylbenzof...

Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan–Yne Cyclization of N-(2-Furanylmethyl) Alkynamides under Air

10.1021/acs.orglett.8b00618

2018-04-09

A protocol for synthesis of chalcone derivatives with a 2-pyridone subunit from N-(2-furanylmethyl) alkynamides is reported. This synthesis involves Pd/Cu-catalyzed oxidative furan–yne cyclization at room temperature in air and may proceed via nucleopalladati...

Pd-Catalyzed Direct C–H Alkenylation and Allylation of Azine N-Oxides

10.1021/acs.orglett.8b00689

2018-04-09

A Pd-catalyzed direct C2-alkenylation of azine N-oxides with allyl acetate is disclosed. The products are formed through an allylation/isomerization cascade process. The use of a tri-tert-butylphosphonium salt as the ligand precursor and KF is mandatory for o...