- PRO-FRAGRANCE COMPOUNDS
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A compound of Formula (I) wherein R1 represents a C3 to C20 hydrocarbon group derived from a fragrant alcohol of formula R1OH or from a fragrant aryl aldehyde or ketone of Formula (II), wherein: R2 is, independently, hydrogen atom, hydroxyl group, acetoxy group, -O(C=O)CH(CH3), optionally substituted C1-C6 alkyl group or C1-C6 alkoxy group, wherein any two of R2 may form an optionally substituted 5 or 6 membered ring, and R1 represents a radical derived from a fragrant alcohol of formula R1OH or from a fragrant aldehyde or from a fragrant aryl aldehyde or ketone of formula (II). The compounds are useful for example as a precursor for the prolonged delivery or release of fragrant compounds such as fragrant alcohols or aldehydes.
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Page/Page column 11; 14
(2014/12/09)
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- Metal-free reductive cleavage of benzylic esters and ethers: Fragmentations result from single and double electron transfers
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The mechanisms for the reductive cleavage of benzylic esters and ethers by neutral organic electron donor 1 are different (see scheme). Products isolated from the cleavage of benzylic ethers result from the transfer of two electrons, without the intermediacy of benzyl radicals, which are believed to be intermediates in the reductive cleavage of benzylic esters. Copyright
- Doni, Eswararao,O'Sullivan, Steven,Murphy, John A.
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supporting information
p. 2239 - 2242
(2013/03/28)
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- Convergent synthesis of trisubstituted Z -allylic esters by wittig-schlosser reaction
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β-Lithiooxyphosphonium ylides, generated in situ from aldehydes and Wittig reagents, react readily with halomethyl esters to form trisubstituted Z-allylic esters. The methodology was applied to a total synthesis of the geranylgeraniol-derived diterpene (6S,7R,Z)-7-hydroxy-2-((E)-6-hydroxy-4- methylhex-4-enylidene)-6,10-dimethylundec-9-enyl acetate (12).
- Hodgson, David M.,Arif, Tanzeel
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supporting information; experimental part
p. 4204 - 4207
(2010/12/24)
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- Total synthesis of methyl sarcophytoate, a marine natural biscembranoid
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(Chemical Equation Presented) The total synthesis of methyl sarcophytoate (1), a marine natural biscembranoid, has been achieved by the thermal Diels-Alder reaction between the 14-membered dienophile unit, methyl sarcoate (2), and the 14-membered diene unit 64. Methyl sarcoate (2) was prepared using n-BuLi-Bu2Mg-mediated dithiane coupling, Kosugi-Migita-Stille coupling, and Grubbs ring-closing metathesis. The diene unit 64 was prepared using Sharpless asymmetric epoxidation, Grubbs ring-closing metathesis, 6-exo-tet epoxide opening, and n-BuLi-Bu2Mg-mediated Ito-Kodama cyclization. The final Diels-Alder reaction between 2 and 64 proceeded with high site, endo/exo, π-face, and regioselectivities. During this reaction, partial E → Z isomerization at the C4 position was observed.
- Ichige, Takahiro,Okano, Yusuke,Kanoh, Naoki,Nakata, Masaya
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supporting information; experimental part
p. 230 - 243
(2009/04/18)
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- Total synthesis of methyl sarcophytoate
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Together with the improved synthesis of the diene unit 15 of methyl sarcophytoate (1), a biscembranoid marine natural product, the asymmetric total synthesis of 1 was achieved by the thermal Diels-Alder reaction between the dienophile unit, methyl sarcoat
- Ichige, Takahiro,Okano, Yusuke,Kanoh, Naoki,Nakata, Masaya
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p. 9862 - 9863
(2008/02/13)
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- Oxidative deprotection of 1,3-dithiane group using NaClO2 and NaH2PO4 in aqueous methanol
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The 1,3-dithiane group was oxidatively deprotected under the conditions of sodium chlorite, sodium dihydrogenphosphate, and 2-methyl-2-butene in 3:1 methanol-water at room temperature in good yield.
- Ichige, Takahiro,Miyake, Annu,Kanoh, Naoki,Nakata, Masaya
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p. 1686 - 1690
(2007/10/03)
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