The first total synthesis and structural determination of (+)-BE-52440A

Tatsuta, Kuniaki; Suzuki, Yoshikazu; Toriumi, Tatsuya; Furuya, Yoshiaki; Hosokawa, Seijiro

doi:10.1016/j.tetlet.2007.09.039

Cited by 27 publications

(26 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…They are dimers of nanaomycin, bridged with sulfur. [65] Figure 9. Recently, the structure has been deduced through total synthesis.…”

Section: F Pyran C-c and S-bridged Dimeric Pyranonaphthoquinonesmentioning

confidence: 99%

“…[65] L-Rhamnoside (192) was converted into 193 by known literature procedures. [65] L-Rhamnoside (192) was converted into 193 by known literature procedures.…”

Section: Regioselective Epoxy Opening Dimerizationmentioning

confidence: 99%

“…Recently, the structure has been deduced through total synthesis. [65] Figure 9. Structures of BE-52440A (7) and BE-52440B (49).…”

Section: F Pyran C-c and S-bridged Dimeric Pyranonaphthoquinonesmentioning

confidence: 99%

“…In 2007, Tatsuta and co-workers achieved the first total synthesis and structural determination of both enantiomers of BE-52440A (7a and 7b) by an enantiodivergent methodology (Scheme 20). [65] L-Rhamnoside (192) was converted into 193 by known literature procedures. [139][140][141][142][143] Further oxidation with AgO under acidic conditions led to quinone (+)-194. tert-Butylhydroperoxide-mediated stereospecific epoxidation of pyranonaphthoquinone (+)-194 followed by demethylation with BCl 3 furnished 196 [(+)-OM-138 αE], a naturally occurring nanaomycin-type antibiotic.…”

Section: Regioselective Epoxy Opening Dimerizationmentioning

confidence: 99%

See 3 more Smart Citations

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

2016

View full text Add to dashboard Cite

The dimeric pyranonaphthoquinones, “bis versions” of the naphtho[2,3‐c]pyran‐5,10‐dione moiety, comprises a group of antibiotics that have been isolated from a variety of sources including plants, bacteria, fungi, and insects. This review discusses the known naturally occurring dimeric pyranonaphthoquinones, their isolation and bioactivity, and synthetic approaches towards them that have helped to confirm their structures, as well as to resolve structural uncertainties such as stereochemistry. The major focus has been on the synthetic approaches adopted to complete the challenging total synthesis of the natural isolates and analogues.

show abstract

“…They are dimers of nanaomycin, bridged with sulfur. [65] Figure 9. Recently, the structure has been deduced through total synthesis.…”

Section: F Pyran C-c and S-bridged Dimeric Pyranonaphthoquinonesmentioning

confidence: 99%

“…[65] L-Rhamnoside (192) was converted into 193 by known literature procedures. [65] L-Rhamnoside (192) was converted into 193 by known literature procedures.…”

Section: Regioselective Epoxy Opening Dimerizationmentioning

confidence: 99%

“…Recently, the structure has been deduced through total synthesis. [65] Figure 9. Structures of BE-52440A (7) and BE-52440B (49).…”

Section: F Pyran C-c and S-bridged Dimeric Pyranonaphthoquinonesmentioning

confidence: 99%

Section: Regioselective Epoxy Opening Dimerizationmentioning

confidence: 99%

See 2 more Smart Citations

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

2016

View full text Add to dashboard Cite

show abstract

“…nanaomycin antibiotics 5), efforts were also made toward the epoxidation of (dihydro)benzo[g]isochromene-5,10-diones 13/14. This goal was realized by reaction of both substrates with H 2 O 2 (32% aqueous solution, 62 equiv) in CH 2 Cl 2 in the presence of Na 2 CO 3 (5 equiv), as an alternative for the tert-butyl hydrogen peroxide-based procedure described in the literature, 23 affording novel epoxybenzo[g]isochromene-5,10-diones 15a-c and 3,4-dihydroepoxybenzo[g]isochromene-5,10-diones 16a-c in acceptable yields (Scheme 2). These epoxidation reactions are presumed to involve initial Michael addition of the hydroperoxide anion across the quinone system followed by enolate-induced cyclization with concomitant hydroxide displacement.…”

mentioning

confidence: 99%

Synthesis and anticancer properties of new (dihydro)pyranonaphthoquinones and their epoxy analogs

Thi

Phương

et al. 2015

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

1,4-Dihydroxy-2-naphthoic acid was used as a substrate for a straightforward five-step synthesis of 3-substituted 1H-benzo[g]isochromene-5,10-diones, with a Michael addition of N-acylmethylpyridinium ylides across 2-hydroxymethyl-1,4-naphthoquinone and a subsequent acid-mediated dehydratation of intermediate hemiacetals as the key steps. The obtained benzo[g]isochromene-5,10-diones were subsequently deployed for further synthetic elaboration to produce new 3,4-dihydrobenzo[g]isochromene-5,10-diones and (3,4-dihydro-)4a,10a-epoxybenzo[g]isochromene-5,10-diones. All compounds were screened for their cytotoxic and antimicrobial effects, revealing an interesting cytotoxic activity of 1H-benzo[g]isochromene-5,10-diones against different cancer cell lines.

show abstract