Photochemistry of latifolin and some related compounds

Walia, Suresh; Kulshrestha, S.K.; Mukherjee, Sabuj

doi:10.1016/s0040-4020(01)82062-7

Cited by 8 publications

(2 citation statements)

References 8 publications

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“…On irradiation in benzene solution and in the absence of a sensitizer, latifolin readily yields the cyclopropane derivative 49. In this case, only the trans isomer was isolated, 39 whereas the irradiation of similar compounds under the same reaction conditions yielded mixtures of cis/trans isomers of the corresponding cyclopropane derivatives.…”

Section: Reaction Centers Arranged In An Acyclic Systemmentioning

confidence: 96%

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Riguet¹,

Hoffmann²

2014

Comprehensive Organic Synthesis II

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Section: Reaction Centers Arranged In An Acyclic Systemmentioning

confidence: 96%

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Riguet¹,

Hoffmann²

2014

Comprehensive Organic Synthesis II

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“…[3][4][5] However, a significant and related work on photochemistry of medicinally or biologically active compounds from plants is sporadic. [6][7][8][9] Several natural plant extract containing terpenoids are widely used in agriculture and medicine. 10,11 Photochemical study is expected to through light on improving the stability of these compounds into the biological formulations made from the natural plant extracts containing terpenoids.…”

Section: Introductionmentioning

confidence: 99%

Photomediated transformation of eremophilanes-I: Photooxidation of 2ß-angeloyloxy-10ß-H-furanoeremophilane

Iqbal¹,

Gupta²,

Husain³

2006

Arkivoc

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The photochemical oxygenation reaction of 2β-angeloyloxy-10β-H-furanoeremophilane (1), a sesquiterpene, was studied in benzene and methanol. Three photoproducts were isolated and characterized by IR 1 H-NMR, 13 C-NMR and mass spectral studies. Sesquiterpene itself was found to be singlet oxygen ( 1 O 2 ) sensitizer. Addition of rose bengal increased the rate of photooxidation whereas as DABCO was found to decrease the rate of photolysis proving the involvement of 1 O 2 in these photoreactions. 2β-Angeloyloxy-8-hydroxy-10β-Heremophilanolide (4) and 2β-angeloyloxy-7,8-epoxy-10β-H-eremophilanolide (6) were obtained as products in benzene. Photolysis in methanol gave a single product 2β-angeloyloxy-10β-H-8-methoxy-12-hydroperoxy-dihydro-furanoeremophilane (7), which was further transformed into product 4, 8 and 12. Reaction was also carried out by adsorbing compound (1) on silica gel bound rose bengal, which yielded the products 4 and 6 with an increase in the rate of reaction.

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Simmons‐Smith Cyclopropanation Reaction

2001

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Almost 30 years after Emschwiller prepared IZnCH 2 I, Simmons and Smith discovered that the reagent formed by mixing a zinc‐copper couple with CH 2 I 2 in ether could be used for the stereospecific conversion of alkenes to cyclopropanes. Nowadays, the Simmons‐Smith cyclopropanation reaction is one of the most widely used reactions in the organic chemist's arsenal for the conversion of olefins into cyclopropanes. This popularity is mainly due to the stereospecificity of the reaction with respect to the double bond geometry and its compatibility with a wide range of functional groups. The chemoselectivity of the reaction toward some olefins is excellent and very few side reactions are observed with functionalized substrates. The metal carbenoid is electrophilic in nature and electron‐rich alkenes usually react much faster than electron‐poor alkenes. Furthermore, the ability to use proximal hydroxy or ether groups to dictate the stereochemical outcome of the CC bond forming process was recognized early on, and this unique property has been successfully exploited on numerous occasions. It has been recognized that halomethylmetal reagents are powerful synthetic tools for the stereoselective addition of a methylene unit to chiral acyclic allylic alcohols and allylic ethers. In addition, the use of halomethylzinc reagents in the presence of chiral additives is one of the few ways to cyclopropanate allylic alcohols efficiently and with good enantiocontrol. Carbenoids can be divided into the following two classes: (1) those of general structure MCH 2 X and (2) those corresponding to M = CH 2 . This chapter is focussed exclusively on the first class in which M = Zn, Sm, or Al. Although other metal carbenoids of type MCH 2 X, such as those derived from Cu, Cd, Hg, and In, have been reported to be effective reagents for the cyclopropanation of some olefins, they have been used only sporadically, and this review does not highlight these reactions. This chapter covers cyclopropanation reactions involving haloalkylzinc, aluminum, and samarium reagents published since the comprehensive chapter in Organic Reactions by Simmons that surveyed the literature up to 1973.

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Photochemistry of latifolin and some related compounds

Cited by 8 publications

References 8 publications

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

5.06 Di-π-methane, Oxa-di-π-methane, and Aza-di-π-methane Photoisomerization

Photomediated transformation of eremophilanes-I: Photooxidation of 2ß-angeloyloxy-10ß-H-furanoeremophilane

Simmons‐Smith Cyclopropanation Reaction

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