Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A

Ford, Paul W.; Narbut, Mathew R.; Belli, Jack; Davidson, Bradley S.

doi:10.1021/jo00099a026

Cited by 75 publications

(48 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…57 Reaction of nitromethane with various aromatic aldehydes in the presence of ammonium acetate under heating (Scheme 4) afforded the respective nitroolefins 4a-g in 65-89% yields, after recrystallization ( Figure 2). …”

Section: Solventless Cfc Reactions Of Indoles With Nitrostyrenesmentioning

confidence: 99%

Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins

Schwalm¹,

Ceschi²,

Russowsky³

2011

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

O were investigated as mild Lewis acids catalysts for the conjugate Friedel-Crafts reaction between indoles and activated olefins. The reactions were carried out with aliphatic unsaturated ketones over a period of days at room temperature, while chalcones reacted only under reflux conditions. The reactions with nitrostyrenes were either performed in solvent or under solventless conditions. In all cases reasonable to good yields were obtained.

show abstract

Section: Solventless Cfc Reactions Of Indoles With Nitrostyrenesmentioning

confidence: 99%

Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins

Schwalm¹,

Ceschi²,

Russowsky³

2011

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…Varacin and Lissoclinotoxin A, the first benzo- [1,2,3,4,5]pentathiepins obtained from marine ascidian, are known for their antitumor and antifungal activities ( Fig. 1) [1,2].…”

Section: Introductionmentioning

confidence: 99%

“…

ABSTRACT: Optically active 4,benzo [1,2,3]trithiole 5-oxide (3) and 4,9-diethyl[1,4]dithiino [5,6-f]benzo [1,2,3]trithiole 5, 8-dioxide (4) were obtained by the asymmetric oxidation of 6,11-diethyl[1,4]dithiino [5,6-h]benzo-[1,2,3,4,5]pentathiepin (1). The reaction was accompanied by desulfurization and ring-contraction reactions of the pentathiepin ring.

…”

mentioning

confidence: 99%

See 1 more Smart Citation

Preparation, structure, and optical properties of chiral sulfoxides and disulfoxide with a trithiole ring

Kimura¹,

Hanzawa²,

Ogawa³

et al. 2003

Heteroatom Chemistry

View full text Add to dashboard Cite

Optically active 4,benzo [1,2,3]trithiole 5-oxide (3) and 4,9-diethyl[1,4]dithiino [5,6-f]benzo [1,2,3]trithiole 5, 8-dioxide (4) were obtained by the asymmetric oxidation of 6,11-diethyl[1,4]dithiino [5,6-h]benzo-[1,2,3,4,5]pentathiepin (1). The reaction was accompanied by desulfurization and ring-contraction reactions of the pentathiepin ring. Similarly, optically active 4,3]dithiolo [4,5-f]benzo-[1,2,3]trithiole 5-oxide (7) was produced by the analogous asymmetric oxidation of 6,10-diethyl-[1,3]dithiolo [4,5-h]benzo [1,2,3,4,5] pentathiepin (2).The specific rotations of 3, 4, and 7 were measured in chloroform, and their optical purity was verified by 1 H NMR with a shift reagent [Eu(hfc) 3 ]. The structures of 4 and 7 were determined by X-ray crystallography using Cu K␣ radiation, and the absolute configuration of the sulfinyl group was examined based on the Flack parameter, which revealed that 4 has an RR configuration, while 7 has an S configuration. The circular

show abstract

“…Cyclic benzopolychalcogenides such as benzopentathiepins [1][2][3][4], benzotetrathiins [5], and benzotrithioles [6][7] have been studied by many heteroatom chemists in fields of synthetic, structural, and biological chemistry [8][9][10][11][12] (Fig. 1).…”

mentioning

confidence: 99%

Heteroatom chemistry of cyclic benzopolychalcogenides: Synthesis and characterization

Sato

2002

Heteroatom Chemistry

View full text Add to dashboard Cite

show abstract

Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A

Cited by 75 publications

References 1 publication

Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins

Metal halide hydrates as lewis acid catalysts for the conjugated friedel-crafts reactions of indoles and activated olefins

Preparation, structure, and optical properties of chiral sulfoxides and disulfoxide with a trithiole ring

Heteroatom chemistry of cyclic benzopolychalcogenides: Synthesis and characterization

Contact Info

Product

Resources

About