Macrocyclic musk compounds—XI

Mamdapur, V. R.; Pai, P. P.; Chakravarti, K.K.; Nayak, U. G.; Bhattacharyya, S.C.

doi:10.1016/s0040-4020(01)90838-5

Cited by 14 publications

(4 citation statements)

References 43 publications

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“…'H-NMR: 1.78 (s, CH,-C(Z')); 2.50 (d, J = 7.5, 2 H-C(1')); 2.65 (m. 2 CH,S); 3.41, 3.50, 3.73, 3.87 (4m, 2 CH,O); 4.21 (t, J = 7.2, H-C(3')). MS: 302 (I, M + ) , 85 (IOO), 119 (53), 43 (20), 67 (15), 57 (14).…”

Section: (Z)-l-bromo-2-mefhyl-5-[(tefrahydro-2h-pyran-2-yl)osy]pent-2mentioning

confidence: 99%

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Structure and Synthesis of Novel C₁₂ Terpenoids from Quince Fruit (Cydonia oblonga MILL.)

Escher

Niclass

1991

Helvetica Chimica Acta

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The structure and synthesis of novel irregular C,, terpenoids isolated from quince fruit (Cydoniu oblonga MILL.) are described: quince oxepine ( = (E)-2,3,6,7-tetrahydro-4-methyl-2-(3-methylbuta-1,3-dienyl)oxepine; 3) and the quince oxepanes as a 1:l mixture of cis-and trans-isomers ( = c i s -and trans-(E)-4-methyl-2-(3-methylbuta-l,3-dienyl)oxepane; 4 and 5, resp.). The absolute configurations of the natural compounds have not been determined due to the minute amounts available, but both relative and absolute configurations of synthetic 4 and 5 were established by chemial correlation with (R)-pulegone.Introduction. -The ripe fruit of quince (Cydoniu oblongu MILL.) imparts a powerful and characteristic flavor and is appreciated for preparing marmalade, candied fruit, sweets, and brandy. The volatile constituents have been extensively analyzed and investigated [I]. The list of compounds identified includes saturated and unsaturated esters and C,, constituents from carotene degradation. A series of C,, constituents of irregular

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Section: (Z)-l-bromo-2-mefhyl-5-[(tefrahydro-2h-pyran-2-yl)osy]pent-2mentioning

confidence: 99%

“…4-Methyl-6-oxohexyl Acetate (15). A s o h of citronella1 dimethyl acetal(l6; 55.5 g, 275 mmol; prepared from rac-citronella1 according to [20]) in MeOH (550 ml), was treated at -75O with a stream of ozone for 3.5 h (4.5 g 03/h, 328 mmol). The excess of ozone was flushed off with Ar.…”

Section: (E)-2367-tetrahydro-4-methyl-2-(3-methylbuta-l3-dienyl)omentioning

confidence: 99%

Structure and Synthesis of Novel C₁₂ Terpenoids from Quince Fruit (Cydonia oblonga MILL.)

Escher

Niclass

1991

Helvetica Chimica Acta

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“…In other syntheses, the aldehyde of citronellal has been protected 1 as the dimethylacetal 6 13 or as the ethylene ketal 14 whilst the acid is often used as its methyl ester.…”

Section: Synthons Derived From Citronellolmentioning

confidence: 99%

“…In some instances, the citronellol or citronellal has been incorporated intact in the syntheses and the isopropyl group has then been removed by ozonolysis to reveal an aldehyde for further modification. Some of the many examples of the use of these compounds in synthesis include muscone, 13 the dolichodials, 14 multistriatin, l7 the Californian red scale insect pheromone, 11 the trigodermols, 20 11,17-dimethyl hentriacontane, 21 4,8-dimethyldecanal, 12 5,9-dimethylpentadecane, 22 the sex pheromone of the German cockroach, 23 6-methyl-2-octadecanone, 24 the sex pheromone of the citrus pest Aondiella citrina, 9 a Puloania bagworm pheromone, 25 and the Phytophthora mating hormone. 26 In several of these examples, the use of the chiral synthon played an important role in establishing the absolute stereochemistry of the bioactive compound.…”

Section: Synthons Derived From Citronellolmentioning

confidence: 99%

Chiral Acylic Synthetic Intermediates from Readily Available Monoterpenoids

Hanson

2015

Journal of Chemical Research

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Eine chiral ökonomische Totalsynthese von (R)‐ und (S)‐Muskon via Epoxysulfoncyclofragmentierung

Branca

Fischli

1977

Helvetica Chimica Acta

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A chiral economic synthesis of (R)-and (S)-muscone using the cyclofragmentation of epoxysulfones SummaryStarting with isobutyric acid (2) and using a microbiological oxidation with pseudomonas putida (S)-8-hydroxy-iso-butyric acid (3) has been prepared. Oxidation of 12 with peracid produced a mixture of the two epoxy-sulfones 13 and 14 (cf. scheme 6). The olefin-derivative 24 was oxidized to the corresponding mixture of 25 and 26. A one pot cyclofragmentation (cJ [4] and scheme 6) produced a mixture of (E)-and (Z)-3-methylcyclopentadec-4-en-1-one (13+ 14 --f 15+ 16, 25+ 26 --f 27

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Macrocyclic musk compounds—XI

Cited by 14 publications

References 43 publications

Structure and Synthesis of Novel C₁₂ Terpenoids from Quince Fruit (Cydonia oblonga MILL.)

Structure and Synthesis of Novel C₁₂ Terpenoids from Quince Fruit (Cydonia oblonga MILL.)

Chiral Acylic Synthetic Intermediates from Readily Available Monoterpenoids

Eine chiral ökonomische Totalsynthese von (R)‐ und (S)‐Muskon via Epoxysulfoncyclofragmentierung

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Macrocyclic musk compounds—XI

Cited by 14 publications

References 43 publications

Structure and Synthesis of Novel C12 Terpenoids from Quince Fruit (Cydonia oblonga MILL.)

Structure and Synthesis of Novel C12 Terpenoids from Quince Fruit (Cydonia oblonga MILL.)

Chiral Acylic Synthetic Intermediates from Readily Available Monoterpenoids

Eine chiral ökonomische Totalsynthese von (R)‐ und (S)‐Muskon via Epoxysulfoncyclofragmentierung

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Product

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Structure and Synthesis of Novel C₁₂ Terpenoids from Quince Fruit (Cydonia oblonga MILL.)

Structure and Synthesis of Novel C₁₂ Terpenoids from Quince Fruit (Cydonia oblonga MILL.)