The indole ring system is present in many natural products, pharmaceuticals, agrochemicals, and other compounds of importance.1–8 The indole unit forms the basis for general BIM and TIM structures (Figure 1). The main purpose of this review is to provide a comprehensive summary of the various synthetic strategies to synthesize BIMs and TIMs. A number of BIM and TIM applications will be briefly pointed out, although this is not the main aim of this review. Many of the most important BIMs and TIMs were widely isolated from various terrestrial and marine natural sources. These natural products have novel structures and exhibit a range of important biological activities.9–19 Cancer chemotherapy with bis(3-indolyl)methane was recently reviewed and numerous activities are reported.20 3,3′-Diindolylmethane and derivatives also are used as dietary supplements for humans.21–24 BIMs inhibit bladder cancer growth,25 inhibit renal cell carcinoma growth,26 have growth inhibitory activity on lung cancer cells,27 are active against colon cancer,28,29 inhibit mammary tumor growth,30,31 induce apoptosis in prostate cancer,32–34 inhibit the proliferation process in breast tumor cells,35–50 have growth inhibitory activity on prostate cancer cell lines,51,52 have antitumorigenic activity,53 serve as topoisomerase IIR catalytic inhibitors,54 serve as inhibitors of the platelet-derived growth factor receptor kinase,55 exhibit antimicrobial and antifungal activities,56,57 exhibit antibiotic activity58 and antibacterial activity,59 have inhibitory effects on phenobarbital-induced hepatic CYP mRNA expression,60 serve as cytodifferentiating agents,61 are antiangiogenic and cytotoxic agents,62 have antimetastatic activity,63 have radical scavenging activity,64 growth promoting activity,65 and analgesic and anti-inflammatory activities,66 and are also utilized as tranquilizers67 and glass-forming high-tripletenergy materials.68 The oxidized form of BIMs and TIMs are utilized as dyes,69–74 as well as colorimetric sensors.75–78 A patent79,80 disclosed the synthetic method of chromogenic 3,3′-bisindolyl-4-azaphthalides 1 and their uses as color formers in pressureand heat-sensitive recording materials (Figure 2).81 A recent patent describes the synthesis of BIMs forming complexes 2 with radioactive metal ions (Gd3+), which are useful contrast agents for radio-imaging and visualization of various tissues and organs (Figure 2).82 Recently Maciejewska et al.83 used DNA-based electrochemical biosensors to demonstrate that bis(5-methoxyindol3-yl) methane, 3,84 considerably reduces the growth of cancer cell lines such as HOP-92 (lung), A498 (renal), and MDAMB-231/1TCC (breast) (Figure 3). Their results also indicate that BIMs could potentially be applied as chemotherapeutic agents against tumors.83,85 Recently Lee and co-workers have found that 1,1,3-tri(3indolyl)cyclohexane, 4, inhibits cancer cell growth in lung cancer cells of xenograft models (Figure 4).86 Ghaedi et al.87,88 have used BIMs coated on an aluminasodium dodecyl sulfate (SDS) surface for preconcentration and determination of Cu(II), Zn(II), Pb(II), and Fe(III) ions by flame atomic absorption spectrometry. Also BIMs and TIMs have been used as ligands for the synthesis of more complex molecules, and different properties of these complexed molecules have been investigated.89–94 † This paper is dedicated to Prof. Dr. Junes Ipaktschi on occasion of his 70th birthday. * To whom correspondence should be addressed. Fax: +98 21 88041344. E-mail: mshiri@alzahra.ac.ir. ‡ Alzahra University. § Bu-Ali Sina University. ⊥ University of KwaZulu-Natal. Figure 1. The structure of BIMs and TIMs. Chem. Rev. 2010, 110, 2250–2293 2250

Bis- and Trisindolylmethanes (BIMs and TIMs)†

The stereospecific ring-opening of O-heterocycles to provide acyclic alcohols and carboxylic acids with controlled formation of a new C–C bond is reported. These reactions provide new methods for synthesis of acyclic polyketide analogs with complex stereochemical arrays. Stereoselective synthesis of the cyclic template is utilized to control relative configuration; subsequent stereospecific nickel-catalyzed ring-opening affords the acyclic product. Aryl-substituted tetrahydrofurans and tetrahydropyrans undergo nickel-catalyzed Kumada-type coupling with a range of Grignard reagents to furnish acyclic alcohols with high diastereoselectivity. Enantioenriched lactones undergo Negishi-type cross-coupling with dimethylzinc to afford enantioenriched carboxylic acids. Application in a two-step enantioselective synthesis of an anti-dyslipidemia agent is demonstrated.

/pdf/stereospecific-cross-coupling-reactions-of-aryl-substituted-5bgz08ypob.pdf

Stereospecific cross-coupling reactions of aryl-substituted tetrahydrofurans, tetrahydropyrans, and lactones.

Terminal alkene substrates can be converted to methyl ketone products via a palladium-catalyzed process known as the Wacker oxidation. This process has found widespread application in targeted synthesis, since alkene substrates are easily accessed and unreactive under diverse reaction conditions substrates and the resultant carbonyl products are common precursors for diverse synthetic manipulations.



This chapter covers the application of the Wacker oxidation and variations of the Wacker oxidation to various types of alkene substrates. The literature covered spans the inception of the reaction in 1959 through November 2012.



A discussion of the current mechanistic understanding is presented, emphasizing considerations that are relevant to synthetic application, including how the nature of the alkene substrate and nucleophiles other than water are proposed to influence the mechanistic pathways and ultimately the product distribution. The “Scope and Limitations” section is separated into discussions relating to functional group tolerance, the influence of heteroatoms proximal to the alkene substrate, and Wacker-type oxidations that do not result in carbonyl products, such as cyclization reactions and aza-Wacker reactions. Select applications of the Wacker oxidation in total synthesis are presented, as well as a comparison to other methods and examples of experimental conditions.


Keywords:

Wacker oxidation(s);
palladium-catalyzed;
nucleopalladation;
oxypalladation;
alkene(s);
olefin(s);
ketone(s);
Markovnikov addition;
anti-Markovnikov addition;
ligand-modulation;
molecular oxygen;
tert-butylhydroperoxide;
Benzoquinone;
allylic alcohol(s);
homoallylic alchol(s);
allylic amine(s);
homoallylic amine(s);
Wacker cyclization;
acetal(s);
aza-Wacker

Wacker Oxidation, The

Stereoselective total synthesis of (+)-anamarine via cross-metathesis protocol

A variety of aldehydes and ketones react rapidly with indoles in the presence of boric acid under solvent-free conditions to afford the corresponding bis(indolyl)methanes. Excellent yields and short reaction times together with the environmentally friendly nature of boric acid make this procedure useful and attractive to produce a variety of bis(indolyl)methanes. The use of boric acid makes it quite simple, more convenient, and practical. This new method offers several advantages such as high conversions, cleaner reaction profiles, short reaction times, and the use of inexpensive and readily available boric acid.

A practical synthesis of bis(indolyl)methanes employing boric acid

Stereoselective Routes for the Total Synthesis of (+)‐Cryptocarya Diacetate

A stereoselective and convergent approach to the total synthesisof the natural product passifloricin A is illustrated using Prinscyclisation and metathesis reactions as key steps.

Convergent Synthesis of PassifloricinA via a Prins Cyclisation and Olefin Cross-Metathesis Approach

Efficient Synthesis of Bis(indolyl)methanes Using Nano Ceria Supported on Vinyl Pyridine Polymer at Ambient Temperature

Efficient Synthesis of Bis(indolyl)methanes Using Nano Ceria Supported on Vinyl Pyridine Polymer at Ambient Temperature.

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Stereoselective Routes for the Total Synthesis of (+)‐Cryptocarya Diacetate

Convergent Synthesis of PassifloricinA via a Prins Cyclisation and Olefin Cross-Metathesis Approach

Efficient Synthesis of Bis(indolyl)methanes Using Nano Ceria Supported on Vinyl Pyridine Polymer at Ambient Temperature

Efficient Synthesis of Bis(indolyl)methanes Using Nano Ceria Supported on Vinyl Pyridine Polymer at Ambient Temperature.