Thiele acetylation of quinones. Part II. p-Benzoquinones with halogen substituents

Blatchly, J. M.; McOmie, J. F. W.; Searle, J. B.

doi:10.1039/j39690001350

Cited by 8 publications

(11 citation statements)

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“…1 H NMR (CDCl 3 , 500 MHz) δ: 1.08 (s, 3H), 1.19 (s, 3H), 1.38 (s, 3H), 1.50-1.60 (m, 2H), 1.62-1.69 (m, 2H), 1.93 (br s, 1H), 1.99 (t, J ) 6.2 Hz, 2H), 5.42 (s, 1H), 7.21 (ddd, J ) 7.5, 7.5, 0.9 Hz, 2H), 7.32 (dd, J ) 7.6, 7.5 Hz, 2H), 7.43 (dd, J ) 7.6, 0.9 Hz, 1H). 13 C NMR (CDCl 3 , 125 MHz) δ: 19.3 (CH 2 ), 21.6 (CH 3 ), 28.6 (CH 3 ), 28.9 (CH 3 ), 33.6 (CH 2 ), 34.8 (C), 39.7 (CH 2 ), 70.7 (CH), 125.9 (2CH), 126.1 (CH), 128.0 (2CH), 133.8 (C), 140.4 (C), 144.9 (C). IR (film): 3424, 1664, 1602, 1493, 1451, 1363, 1311, 1217, 1031, 974, 753 cm -1 .…”

Section: Methodsmentioning

confidence: 99%

A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H

et al. 2009

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A very expedient and efficient new route toward taiwaniaquinoids, bearing the 4a-methyltetrahydrofluorene skeleton, is reported. Key steps are the intramolecular Friedel-Crafts alkylation of an aryldiene and the degradative oxidation of a methylenedioxy group; the latter process could also be utilized for building the 2-hydroxy-1,4-benzoquinone unit, which is frequently found in natural products. Utilizing this new methodology, (+/-)-dichroanone (7) (three steps, 77% overall yield) and (+/-)-taiwaniaquinone H (6) (four steps, 70% overall yield) have been synthesized from commercial alpha- (11a) or beta-cyclocitral (11b).

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Section: Methodsmentioning

confidence: 99%

A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H

et al. 2009

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“…Fractions containing the product spot (TLC) were pooled and evaporated under reduced pressure to afford 21h (156 mg, 63%) as off-white lustrous solid, TLC R f 0.2 (ethyl acetate/hexanes, 1:5); mp 51.6–52.2 °C (lit. 30 mp 54.0–55.5 °C); 1 H NMR (CDCl 3 ): 3.92–4.0 (m, 9 H, OC H 3 ), 6.6 (s, 1 H, C 6 H 2 ), 7.1 (s, 1 H, C 6 H 2 ).…”

Section: Methodsmentioning

confidence: 99%

“…29–31 Thus, compounds 21g and 21h were synthesized by regioselective bromination (Scheme 3). 29, 30 While 21i was synthesized from 25 by a Dakin reaction 31 followed by methylation.…”

Section: Chemistrymentioning

confidence: 99%

2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzyl-pyrrolo[2,3-d]pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance

Gangjee

Namjoshi

Keller

et al. 2011

Bioorganic & Medicinal Chemistry

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Gangjee et al. recently reported a novel series of 2-amino-4-methyl-5-phenylethyl substituted-7-benzyl-pyrrolo[2,3-d]pyrimidines, some of which exhibited two digit nanomolar antitumor and antimitotic activity and were not subject to P-glycoprotein (Pgp) or Multidrug Resistance Protein 1 (MRP1) mediated tumor resistance (unlike the Vinca alkaloids and taxanes). Some of these compounds, in addition to their antitumor activity, had the ability to reverse the Pgp-mediated resistance to clinically used antimitotic agents. This report consists of an attempt to optimize the various activities of the parent compounds by synthetic variations of the phenyl ring of the 5-phenylethyl side chain. The target compounds were synthesized via a 9-step synthesis involving a Sonogashira reaction. The substituted phenylacetylenes as coupling partners were in turn synthesized from unactivated aryl bromides or iodides. The target compounds exhibited moderate cytotoxicity against MCF-7 tumor cells. However, most of these compounds showed improved cytotoxicity against the resistant NCI/ADR and MCF-7/VP. This study afforded an analog which reversed both Pgp-mediated as well as MRP1-mediated resistance to clinically used antimitotic agents, along with its own antimitotic mediated antitumor activity. In addition, in the NCI-60 cell line panel one of the compounds inhibited the growth of MDA-MD-435 breast cancer cell line at submicromolar concentration.

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“…Finally its oxidation produced the spiro compound 139 as a diastereomeric mixture (1 : 1) [15b] . Regioisomeric dienes 140 and 141 were synthesized based on the reported procedure [15c] . With diene and dienophiles in hand, [4+2] cycloaddition of 139 with the substrates 140 and 141 gave the cycloadducts ( R )‐ 142 and ( S )‐ 143 respectively under the similar reaction conditions.…”

Section: Various Synthetic Routes By Different Groups In the Total Sy...mentioning

confidence: 99%

Synthetic Approaches to the Anticancer Agent Fredericamycin A

Kotha

Fatma

2020

Asian J Org Chem

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In this minireview, we have highlighted various developments related to the total synthesis of an anticancer agent, fredericamycin A (NSC-305263). The presence of a unique molecular architecture and significant biological properties associated with fredericamycin A have greatly enhanced the research activity, and we cover the total synthesis of this molecule since its isolation. Different methodologies adopted for the construction of the stereo-genic spiro centre are radical spirocyclization, Diels À Alder (DA) reaction, [3 + 2] annulation, photochemical approach, ring-closing metathesis (RCM), palladium-catalyzed crosscoupling reaction, rearrangement approach, benzannulation etc. This minireview provides an overview of the contribution of different research groups in the total synthesis of fredericamycin A. We also cover various model studies related to the synthesis of this molecule.

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Thiele acetylation of quinones. Part II. p-Benzoquinones with halogen substituents

Cited by 8 publications

References 0 publications

A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H

A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H

2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzyl-pyrrolo[2,3-d]pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance

Synthetic Approaches to the Anticancer Agent Fredericamycin A

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