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Volumn 67, Issue 10, 2003, Pages 2210-2214

Synthesis of the racemate and both enantiomers of massoilactone

Author keywords

(R) (+) 1,2 epoxyheptane; Flavor; Massoilactone; Mitsunobu inversion

Indexed keywords

ALDEHYDE; FLAVORING AGENT; LACTONE; N HEXANAL; N-HEXANAL;

EID: 3142728083     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.67.2210     Document Type: Article
Times cited : (14)

References (33)
  • 1
    • 0000601168 scopus 로고
    • The main component of the essential oil of massooi. Part I
    • Abe, S., The main component of the essential oil of massooi. Part I. J. Chem. Soc. Japan, 58, 246-248 (1937).
    • (1937) J. Chem. Soc. Japan , vol.58 , pp. 246-248
    • Abe, S.1
  • 2
    • 0001629693 scopus 로고
    • Insect venoms, attractants, and repellents
    • Cavill, G. W. K., Clark, D. V., and Whitfield, F. B., Insect venoms, attractants, and repellents. Aust. J. Chem., 21, 2819-2823 (1968).
    • (1968) Aust. J. Chem. , vol.21 , pp. 2819-2823
    • Cavill, G.W.K.1    Clark, D.V.2    Whitfield, F.B.3
  • 3
    • 0002143918 scopus 로고
    • Constituents of cane molasses. Part III. Isolation and identification of (-)-2-deceno-5-lactone (massoialactone)
    • Hashizume, T., Kikuchi, N., Sasaki, Y., and Sakata, I., Constituents of cane molasses. Part III. Isolation and identification of (-)-2-deceno-5-lactone (massoialactone). Agric. Biol. Chem., 32, 1306-1309 (1968).
    • (1968) Agric. Biol. Chem. , vol.32 , pp. 1306-1309
    • Hashizume, T.1    Kikuchi, N.2    Sasaki, Y.3    Sakata, I.4
  • 4
    • 49549132278 scopus 로고
    • Das lacton der 5-hydroxy-cis-2, cis-7-decadiensaeure und weitere lactone aus dem absolue der blueten von polianthes tuberosa L.
    • Kaiser, R., and Lamparsky, D., Das lacton der 5-hydroxy-cis-2, cis-7-decadiensaeure und weitere lactone aus dem absolue der blueten von polianthes tuberosa L. Tetrahedron Lett., 20, 1659-1660 (1976).
    • (1976) Tetrahedron Lett. , vol.20 , pp. 1659-1660
    • Kaiser, R.1    Lamparsky, D.2
  • 5
    • 0025127519 scopus 로고
    • Enantioselective analysis of dec-2-en-5-olide (massoilactone) from natural sources by multidimensional capillary gas chromatography
    • Bernreuther, A., Lander, V., Huffer, M., and Schreier, P., Enantioselective analysis of dec-2-en-5-olide (massoilactone) from natural sources by multidimensional capillary gas chromatography. Flavour Fragr. J., 5, 71-73 (1990).
    • (1990) Flavour Fragr. J. , vol.5 , pp. 71-73
    • Bernreuther, A.1    Lander, V.2    Huffer, M.3    Schreier, P.4
  • 6
    • 37049152800 scopus 로고
    • Amides of vegetable origin. Part V. Stereochemistry of conjugated dienes. Synthesis of (±)-massoialactone
    • Crombie, L., Amides of vegetable origin. Part V. Stereochemistry of conjugated dienes. Synthesis of (±)-massoialactone. J. Chem. Soc., 1007-1025, 2535 (1955).
    • (1955) J. Chem. Soc. , vol.2535 , pp. 1007-1025
    • Crombie, L.1
  • 7
    • 0009516024 scopus 로고
    • Studies on synthesis of massoi-lactone and its homologues. Part II. Synthesis of nonyn-1-o1-4-carboxylic acid-1-lactone (massoi-lactone)
    • Abe, S., and Sato, K., Studies on synthesis of massoi-lactone and its homologues. Part II. Synthesis of nonyn-1-o1-4-carboxylic acid-1-lactone (massoi-lactone). Bull. Chem. Soc. Japan, 29, 88-90 (1956).
    • (1956) Bull. Chem. Soc. Japan , vol.29 , pp. 88-90
    • Abe, S.1    Sato, K.2
  • 8
    • 0017124291 scopus 로고
    • Absolute configuration of (-)-massoilactone as confirmed by a synthesis of (S)-(+)-isomer
    • Mori, K., Absolute configuration of (-)-massoilactone as confirmed by a synthesis of (S)-(+)-isomer. Agric. Biol. Chem., 40, 1617-1619 (1976).
    • (1976) Agric. Biol. Chem. , vol.40 , pp. 1617-1619
    • Mori, K.1
  • 9
    • 0009551022 scopus 로고
    • Syntheses of unsaturated lactones. Part I. Some lactones of 5-substituted-5-hydroxy-2-enoic acids as a synthetic butter or butter cake flavor
    • Nobuhara, A., Syntheses of unsaturated lactones. Part I. Some lactones of 5-substituted-5-hydroxy-2-enoic acids as a synthetic butter or butter cake flavor. Agric. Biol. Chem., 32, 1016-1020 (1968).
    • (1968) Agric. Biol. Chem. , vol.32 , pp. 1016-1020
    • Nobuhara, A.1
  • 10
    • 0001585193 scopus 로고
    • Synthesis of substituted 5,6-dihydro-2H-pyran-2-ones. Propiolic acid dianion as a reactive three-carbon nucleophile
    • Carlson, R. M., Oyler, A. R., and Peterson, J. R., Synthesis of substituted 5,6-dihydro-2H-pyran-2-ones. Propiolic acid dianion as a reactive three-carbon nucleophile. J. Org. Chem., 40, 1610-1616 (1975).
    • (1975) J. Org. Chem. , vol.40 , pp. 1610-1616
    • Carlson, R.M.1    Oyler, A.R.2    Peterson, J.R.3
  • 11
    • 0000401708 scopus 로고
    • Novel approach to the synthesis of 6-substituted 5,6-dihydro-2(2H)- pyranones
    • Fehr, C., Galindo, J., and Ohloff, G., Novel approach to the synthesis of 6-substituted 5,6-dihydro-2(2H)-pyranones. Helv. Chim. Acta, 64, 1247-1256 (1981).
    • (1981) Helv. Chim. Acta , vol.64 , pp. 1247-1256
    • Fehr, C.1    Galindo, J.2    Ohloff, G.3
  • 12
    • 0006214589 scopus 로고
    • A very simple synthesis of natural saturated δ-substituted δ-lactones. The pheromone of uespa orientalis
    • Bacardit, R., and Moreno-manas, M., A very simple synthesis of natural saturated δ-substituted δ-lactones. The pheromone of uespa orientalis. Chem. Lett., 5-6 (1982).
    • (1982) Chem. Lett. , pp. 5-6
    • Bacardit, R.1    Moreno-manas, M.2
  • 13
    • 0003661771 scopus 로고
    • A new method for synthesis of α,β-unsaturated δ-lactones via Michael addition using methyl (phenylsulfinyl) acetate
    • Yoshida, T., and Saito, S., A new method for synthesis of α,β-unsaturated δ-lactones via Michael addition using methyl (phenylsulfinyl) acetate. Chem. Lett., 1587-1590 (1982).
    • (1982) Chem. Lett. , pp. 1587-1590
    • Yoshida, T.1    Saito, S.2
  • 14
    • 0011983580 scopus 로고
    • A new synthesis of α,β-unsaturated γ- and δ-lactones via intramolecular acylation of α-sulfinyl carbanion
    • Pohmakotr, M., and Jarupan, P., A new synthesis of α,β- unsaturated γ- and δ-lactones via intramolecular acylation of α-sulfinyl carbanion. Tetrahedron Lett., 26, 2253-2256 (1985).
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2253-2256
    • Pohmakotr, M.1    Jarupan, P.2
  • 15
    • 0000794537 scopus 로고
    • Asymmetric reductions of propargyl ketones. An effective approach to the synthesis of optically active compounds
    • Midland, M. M., Tramontano, A., Kazubski, A., Graham, R. S., Tsai, D. J. S., and Cardin, D. B., Asymmetric reductions of propargyl ketones. An effective approach to the synthesis of optically active compounds. Tetrahedron, 40, 1371-1380 (1984).
    • (1984) Tetrahedron , vol.40 , pp. 1371-1380
    • Midland, M.M.1    Tramontano, A.2    Kazubski, A.3    Graham, R.S.4    Tsai, D.J.S.5    Cardin, D.B.6
  • 16
    • 0025350148 scopus 로고
    • Synthesis and utilization of optically active 2-substituted 4-(trimethylsilyl)cyclopentanones: Synthesis of (-)-massoialactone and (+)-β-cuparenone
    • Asaoka, M., Hayashibe, S., Sonoda, S., and Takei, H., Synthesis and utilization of optically active 2-substituted 4-(trimethylsilyl)cyclopentanones: Synthesis of (-)-massoialactone and (+)-β-cuparenone. Tetrahedron Lett., 31, 4761-4764 (1990).
    • (1990) Tetrahedron Lett. , vol.31 , pp. 4761-4764
    • Asaoka, M.1    Hayashibe, S.2    Sonoda, S.3    Takei, H.4
  • 17
    • 37049066736 scopus 로고
    • Total syntheses of natural (+)-(4R, 6R)-4-hydroxy-6-pentylvalerolactone and of (-)-(6R)-massoialactone
    • Bennett, F., Knight, D. W., and Fenton, G., Total syntheses of natural (+)-(4R, 6R)-4-hydroxy-6-pentylvalerolactone and of (-)-(6R)-massoialactone. J. Chem. Soc. Perkin Trans. 1, 1543-1547 (1991).
    • (1991) J. Chem. Soc. Perkin Trans. 1 , pp. 1543-1547
    • Bennett, F.1    Knight, D.W.2    Fenton, G.3
  • 18
    • 0001624567 scopus 로고
    • Secondary metabolites by chemical screening-13. Enantioselective synthesis of δ-lactones from streptenol A, a chiral building block from streptomyces
    • Romeyke, Y., Keller, M., Kluge, H., Grabley, S., and Hammann, P., Secondary metabolites by chemical screening-13. Enantioselective synthesis of δ-lactones from streptenol A, a chiral building block from streptomyces. Tetrahedron, 47, 3335-3346 (1991).
    • (1991) Tetrahedron , vol.47 , pp. 3335-3346
    • Romeyke, Y.1    Keller, M.2    Kluge, H.3    Grabley, S.4    Hammann, P.5
  • 19
    • 0026531491 scopus 로고
    • Enzyme catalyzed lactonization of 3,5-dihydroxy esters: Enantioselective synthesis of naturally occurring 3-hydroxy-5-decanolide, (-)-massoialactone, and 3-hydroxy-5-icosanolide
    • Bonini, C., Pucci, P., Racioppi, R., and Viggiani, L., Enzyme catalyzed lactonization of 3,5-dihydroxy esters: enantioselective synthesis of naturally occurring 3-hydroxy-5-decanolide, (-)-massoialactone, and 3-hydroxy-5- icosanolide. Tetrahedron: Asymmetry, 3, 29-32 (1992).
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 29-32
    • Bonini, C.1    Pucci, P.2    Racioppi, R.3    Viggiani, L.4
  • 20
    • 0026578717 scopus 로고
    • An enantiospecific route to (6R)-(-)-massoialactone and (4R, 6R)-(+)-4-hydroxy-6-pentylvalerolactone
    • Takano, S., Setoh, M., and Ogasawara, K., An enantiospecific route to (6R)-(-)-massoialactone and (4R, 6R)-(+)-4-hydroxy-6-pentylvalerolactone. Tetrahedron: Asymmetry, 3, 533-534 (1992).
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 533-534
    • Takano, S.1    Setoh, M.2    Ogasawara, K.3
  • 21
    • 0027157207 scopus 로고
    • Enzyme assisted synthesis of enantiomerically pure δ-lactones
    • Hasse, B., and Schneider, M. P., Enzyme assisted synthesis of enantiomerically pure δ-lactones. Tetrahedron: Asymmetry, 4, 1017-1026 (1993).
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1017-1026
    • Hasse, B.1    Schneider, M.P.2
  • 22
    • 85034170537 scopus 로고
    • Stereoselective approach to tetrahydropyran by iodoetherifications of (2S, 3S)-2,3-bis(t-butyldimethylsilyloxy)-5-alkene-1-ol
    • Minami, T., Moriyama, A., and Hanaoka, M., Stereoselective approach to tetrahydropyran by iodoetherifications of (2S, 3S)-2,3-bis(t- butyldimethylsilyloxy)-5-alkene-1-ol. Synlett, 663-665 (1995).
    • (1995) Synlett , pp. 663-665
    • Minami, T.1    Moriyama, A.2    Hanaoka, M.3
  • 23
    • 0033584872 scopus 로고    scopus 로고
    • Asymmetric synthesis of (S)-massoialactone
    • Pais, G. C. G., Fernandes, R. A., and Kumar, P., Asymmetric synthesis of (S)-massoialactone. Tetrahedron, 55, 13445-13450 (1999).
    • (1999) Tetrahedron , vol.55 , pp. 13445-13450
    • Pais, G.C.G.1    Fernandes, R.A.2    Kumar, P.3
  • 24
    • 0034728178 scopus 로고    scopus 로고
    • Asymmetric synthesis of goniothalamin, hexadecanolide, massoialactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions
    • Ramachandran, P. V., Reddy, M. V. R., and Brown, H. C., Asymmetric synthesis of goniothalamin, hexadecanolide, massoialactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions. Tetrahedron Lett., 41, 583-586 (2000).
    • (2000) Tetrahedron Lett. , vol.41 , pp. 583-586
    • Ramachandran, P.V.1    Reddy, M.V.R.2    Brown, H.C.3
  • 25
    • 0035136722 scopus 로고    scopus 로고
    • One-pot diastereoselective preparation of α,β-unsaturated- γ-silylated-δ-lactones: Application towards natural compounds
    • Marion, F., Fol, R. L., Courillon, C., and Malacria, M., One-pot diastereoselective preparation of α,β-unsaturated-γ-silylated- δ-lactones: Application towards natural compounds. Synlett, 138-140 (2001).
    • (2001) Synlett , pp. 138-140
    • Marion, F.1    Fol, R.L.2    Courillon, C.3    Malacria, M.4
  • 26
    • 0035832083 scopus 로고    scopus 로고
    • A new chiral route to 5- and 6-substituted hydropyran2-ones utilizing enantiopure 4-cumyloxy-2-cyclopenten-1-one
    • Sato, M., Nakashima, H., Hanada, K., Hayashi, M., Honzumi, M., Taniguchi, T., and Ogasawara, K., A new chiral route to 5- and 6-substituted hydropyran2-ones utilizing enantiopure 4-cumyloxy-2-cyclopenten-1-one. Tetrahedron Lett., 42, 2833-2837 (2001).
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2833-2837
    • Sato, M.1    Nakashima, H.2    Hanada, K.3    Hayashi, M.4    Honzumi, M.5    Taniguchi, T.6    Ogasawara, K.7
  • 27
    • 0001622565 scopus 로고
    • Enantiomerically pure lactones. 3. Synthesis of and stereospecific conjugate additions to α,β-unsaturated lactones
    • Pirkle, W. H., and Adams, P. E., Enantiomerically pure lactones. 3. Synthesis of and stereospecific conjugate additions to α,β- unsaturated lactones. J. Org. Chem., 45, 4117-4121 (1980).
    • (1980) J. Org. Chem. , vol.45 , pp. 4117-4121
    • Pirkle, W.H.1    Adams, P.E.2
  • 28
    • 0031795337 scopus 로고    scopus 로고
    • Optical resolution and application of 1-aminotetralin
    • Konno, Y., Tominaga, T., Murata, T., Aoki, Y., and Nohira, H., Optical resolution and application of 1-aminotetralin. Enantiomer, 3, 181-185 (1998).
    • (1998) Enantiomer , vol.3 , pp. 181-185
    • Konno, Y.1    Tominaga, T.2    Murata, T.3    Aoki, Y.4    Nohira, H.5
  • 29
    • 0000501267 scopus 로고
    • A convenient method for utilizing the allyl Grignard reagent
    • Dreyfuss, M. P., A convenient method for utilizing the allyl Grignard reagent. J. Org. Chem., 28, 3269-3272 (1963).
    • (1963) J. Org. Chem. , vol.28 , pp. 3269-3272
    • Dreyfuss, M.P.1
  • 30
    • 0000706695 scopus 로고
    • The rearrangement of α,β-epoxy ketones. III. The intramolecular nature of the rearrangement
    • House, H. O., The rearrangement of α,β-epoxy ketones. III. The intramolecular nature of the rearrangement. J. Am. Chem. Soc., 78, 2298-2302 (1956).
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 2298-2302
    • House, H.O.1
  • 31
    • 4544247985 scopus 로고
    • Derivatives of epichlorohydrin. III. A new method of preparing γ-alkoxy-γ-butyrolactones
    • Kuwamura, T., and Takahashi, H., Derivatives of epichlorohydrin. III. A new method of preparing γ-alkoxy-γ-butyrolactones. Bull. Chem. Soc. Japan, 42, 1345-1350 (1969).
    • (1969) Bull. Chem. Soc. Japan , vol.42 , pp. 1345-1350
    • Kuwamura, T.1    Takahashi, H.2
  • 32
    • 85077634689 scopus 로고
    • The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products
    • Mitsunobu, O., The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis, 1-28 (1981).
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 33
    • 0034827480 scopus 로고    scopus 로고
    • Development of an efficient GLC system with a mixed chiral stationary phase and its application to the separation of optical isomers
    • Tamogami, S., Awano, K., Amaike, M., Takagi, Y., and Kitahara, T., Development of an efficient GLC system with a mixed chiral stationary phase and its application to the separation of optical isomers. Flavour Fragr. J., 16, 349-352 (2001).
    • (2001) Flavour Fragr. J. , vol.16 , pp. 349-352
    • Tamogami, S.1    Awano, K.2    Amaike, M.3    Takagi, Y.4    Kitahara, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.