A two step biomimetic total synthesis of eilatin

Gellerman, Gari; Babad, Malca; Kashman, Yoel

doi:10.1016/s0040-4039(00)60790-6

Cited by 26 publications

(13 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…16 Ru(bpy) 2 (eilatin) 2+ was synthesized as reported and purified via an ion exchange column (Aldrich Sephadex CM25) and reverse-phase high-performance liquid chromatography [HP1100 HPLC system with Varian DynaMax C18 semipreparative column, gradient of 15:85 TO 60:40 H 2 O (0.1% TFA)/MeCN (0.1% TFA) over 60 min]. 13 No extinction coefficients in buffer have been reported.…”

Section: Metal Complexesmentioning

confidence: 99%

Binding of Ru(bpy)₂(eilatin)²⁺ to Matched and Mismatched DNA

Zeglis

Barton

2008

Inorg. Chem.

View full text Add to dashboard Cite

The DNA-binding properties of Ru(bpy) 2 (eilatin) 2+ have been investigated to determine if the sterically expansive eilatin ligand confers specificity for destabilized single-base mismatches in DNA. Competitive DNA photocleavage experiments employing a sequence-neutral metallointercalator, Rh(bpy) 2 (phi) 3+ (phi = 9,10-phenanthrenequinonediimine), and a mismatchspecific metalloinsertor, Rh(bpy) 2 (chrysi) 3+ (chrysi = chrysene-5,6-quinonediimine), reveal that the eilatin complex binds to a CC mismatched site with an apparent binding constant of 2.2(2) × 10 6 M −1 . Nonetheless, the selectivity in binding mismatched DNA is not high: competitive titrations with Rh(bpy) 2 (phi) 3+ show that the complex binds also to well-matched B-form sites. Thus, Ru (bpy) 2 (eilatin) 2+ , despite containing the extremely expansive eilatin ligand, displays lower selectivity for the mismatch than does Rh(bpy) 2 (chrysi) 3+ , a metalloinsertor containing the smaller, though still bulky, chrysene-5,6-quinonediimine ligand. In summary, the size and shape of the eilatin ligand allow stacking with both well-matched and mismatched DNA.

show abstract

Section: Metal Complexesmentioning

confidence: 99%

Binding of Ru(bpy)₂(eilatin)²⁺ to Matched and Mismatched DNA

Zeglis

Barton

2008

Inorg. Chem.

View full text Add to dashboard Cite

show abstract

“…An alternative route towards eilatin ( 90 ) was accomplished by the treatment of 103 first with BF 3 etherate. The so-obtained pentacyclus 104 was converted to eilatin ( 90 ) under alkaline conditions (NH 3 -MeOH) ( Scheme 17 ) [ 34 ]. No yields were given for the final steps in both approaches.…”

Section: Eilatin-type Pyridoacridinesmentioning

confidence: 99%

“… Biomimetic synthesis of eilatin ( 90 ): ( a ) NaIO 3 , EtOH (15%); ( b ) BF 3 ·OEt 2 , CH 2 Cl 2 (no yield given); ( c ) NH 3 , MeOH (no yield given) [ 34 ]. …”

Section: Eilatin-type Pyridoacridinesmentioning

confidence: 99%

New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

Plodek

Bracher

2016

Marine Drugs

View full text Add to dashboard Cite

Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids. This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades.

show abstract

“…8 A very simple, but low-yielding biomimetic approach towards 1 was reported by Kashman's group. 9 This approach suggests that kynuramine and o-benzoquinone could be biosynthetic precursors of 1. 9 Furthermore, Kashman also described an approach towards 2 starting from a kynuramine derivative and 2,5-dihydroxy-1,4-cyclohexanedione.…”

Section: Figurementioning

confidence: 99%

“…9 This approach suggests that kynuramine and o-benzoquinone could be biosynthetic precursors of 1. 9 Furthermore, Kashman also described an approach towards 2 starting from a kynuramine derivative and 2,5-dihydroxy-1,4-cyclohexanedione. 10 In continuation of our recent efforts on the synthesis of marine pyridoacridine alkaloids and analogues thereof 11 we worked out a new, divergent synthesis of 1 and 2, which substantially differs from the above-mentioned approaches and opens a novel access to pyridoacridine alkaloids.…”

Section: Figurementioning

confidence: 99%