메뉴 건너뛰기




Volumn 37, Issue 10, 2007, Pages 1635-1651

Dibromomethane as one-carbon source in organic synthesis: Formal total synthesis of (±)-nephrosteranic acid

Author keywords

methylenation; methylene butyrolactones; substituted acrolein; cis nephrosterinic acid; Nephrosteranic acid; Paraconic acids

Indexed keywords

ACID; CARBON; DIBROMOMETHANE; NEPHROSTERANIC ACID; UNCLASSIFIED DRUG;

EID: 34249336049     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701263767     Document Type: Article
Times cited : (10)

References (41)
  • 1
    • 37049084069 scopus 로고
    • Preparation of α-substituted acroleins via the reaction of aldehyde with dihalomethane and diethylamine
    • (a) Hon, Y. S.; Chang, F. J.; Lu, L. Preparation of α-substituted acroleins via the reaction of aldehyde with dihalomethane and diethylamine. Chem. Commun. 1994, 2041-2042;
    • (1994) Chem. Commun , pp. 2041-2042
    • Hon, Y.S.1    Chang, F.J.2    Lu, L.3
  • 2
    • 0032516288 scopus 로고    scopus 로고
    • Preparation of α-substituted acroleins via the reaction of aldehyde or the corresponding ozonide with dibromomethane and diethylamine
    • (b) Hon, Y. S.; Chang, F. J.; Lu, L.; Lin, W. C. Preparation of α-substituted acroleins via the reaction of aldehyde or the corresponding ozonide with dibromomethane and diethylamine. Tetrahedron 1998, 54, 5233-5246;
    • (1998) Tetrahedron , vol.54 , pp. 5233-5246
    • Hon, Y.S.1    Chang, F.J.2    Lu, L.3    Lin, W.C.4
  • 3
    • 0037463494 scopus 로고    scopus 로고
    • Dibromomethane as one-carbon source in organic synthesis: Microwave accelerated α-methylenation of ketones with dibromomethane and diethylamine
    • (c) Hon, Y. S.; Hsu, T. R.; Chen, C. Y.; Lin, Y. H.; Chang, F. R.; Hsieh, C. H.; Szu, P. H. Dibromomethane as one-carbon source in organic synthesis: Microwave accelerated α-methylenation of ketones with dibromomethane and diethylamine. Tetrahedron 2003, 59, 1509-1520.
    • (2003) Tetrahedron , vol.59 , pp. 1509-1520
    • Hon, Y.S.1    Hsu, T.R.2    Chen, C.Y.3    Lin, Y.H.4    Chang, F.R.5    Hsieh, C.H.6    Szu, P.H.7
  • 4
    • 0028853803 scopus 로고
    • Preparation of α-keto acid derivatives from terminal alkenes
    • Hon, Y. S.; Lin, W. C. Preparation of α-keto acid derivatives from terminal alkenes. Tetrahedron Lett. 1995, 36, 7693-7696.
    • (1995) Tetrahedron Lett , vol.36 , pp. 7693-7696
    • Hon, Y.S.1    Lin, W.C.2
  • 5
    • 2342620626 scopus 로고    scopus 로고
    • Dibromethane as one-carbon source in organic synthesis: A versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes
    • Hon, Y. S.; Liu, Y. W.; Hsieh, C. H. Dibromethane as one-carbon source in organic synthesis: A versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes. Tetrahedron 2004, 60, 4837-4860.
    • (2004) Tetrahedron , vol.60 , pp. 4837-4860
    • Hon, Y.S.1    Liu, Y.W.2    Hsieh, C.H.3
  • 6
    • 13844298912 scopus 로고    scopus 로고
    • For the total synthesis of (±)- and (-)-methylenolactocin (4): (a) Hon, Y. S.; Hsieh, C. H.; Liu, Y. W. Dibromethane as one-carbon source in organic synthesis: Total synthesis of (±)- and (-)-methylenelactocin. Tetrahedron 2005, 61, 2713-2723, and the references cited therein;
    • For the total synthesis of (±)- and (-)-methylenolactocin (4): (a) Hon, Y. S.; Hsieh, C. H.; Liu, Y. W. Dibromethane as one-carbon source in organic synthesis: Total synthesis of (±)- and (-)-methylenelactocin. Tetrahedron 2005, 61, 2713-2723, and the references cited therein;
  • 7
    • 2342616192 scopus 로고    scopus 로고
    • Recent progress of the preparation of α-keto acid derivatives
    • (b) Hon, Y. S. Recent progress of the preparation of α-keto acid derivatives. Chemistry (Chinese Chem. Soc., Taipei) 1996, 54, 95-102;
    • (1996) Chemistry (Chinese Chem. Soc., Taipei) , vol.54 , pp. 95-102
    • Hon, Y.S.1
  • 8
    • 33748076103 scopus 로고    scopus 로고
    • For the total synthesis of (±)-canadensolide (9), please see Hon, Y. S.; Hsieh, C. H. Dibromethane as one-carbon source in organic synthesis: Total synthesis of (±)-canadensolide. Tetrahedron 2006, 62, 9713-9717, and the references cited therein.
    • (c) For the total synthesis of (±)-canadensolide (9), please see Hon, Y. S.; Hsieh, C. H. Dibromethane as one-carbon source in organic synthesis: Total synthesis of (±)-canadensolide. Tetrahedron 2006, 62, 9713-9717, and the references cited therein.
  • 9
    • 34249292611 scopus 로고    scopus 로고
    • For nephrosteranic acid (10) isolation, see (a) Asahina, Y. Yanagita, M.; Sakurai, Y. Lichen substances, LXXVII: The lichen aliphatic acids from. Nephromopsis endocrocea. Chem. Ber. 1937, 70B, 227-235;
    • For nephrosteranic acid (10) isolation, see (a) Asahina, Y. Yanagita, M.; Sakurai, Y. Lichen substances, LXXVII: The lichen aliphatic acids from. Nephromopsis endocrocea. Chem. Ber. 1937, 70B, 227-235;
  • 10
    • 0347761351 scopus 로고    scopus 로고
    • Desymmetrization of metalated cyclohexadienes and application to the synthesis of nephrosteranic acid
    • For synthesis, see b
    • For synthesis, see (b) Schleth, F.; Studer, A. Desymmetrization of metalated cyclohexadienes and application to the synthesis of nephrosteranic acid. Angew. Chem. Int. Ed. Engl. 2004, 43, 313-315;
    • (2004) Angew. Chem. Int. Ed. Engl , vol.43 , pp. 313-315
    • Schleth, F.1    Studer, A.2
  • 12
    • 0344514156 scopus 로고    scopus 로고
    • Aldol reactions of dioxanes derived from tartaric acid: A total synthesis of (+)-nephrosteranic acid
    • (d) Barros, M. T.; Maycock, C. D.; Ventura, M. R. Aldol reactions of dioxanes derived from tartaric acid: A total synthesis of (+)-nephrosteranic acid. Org. Lett. 2003, 5, 4097-4100;
    • (2003) Org. Lett , vol.5 , pp. 4097-4100
    • Barros, M.T.1    Maycock, C.D.2    Ventura, M.R.3
  • 13
    • 0037155527 scopus 로고    scopus 로고
    • Free-radical-mediated conjugate additions: Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid
    • (e) Sibi, M. P.; Liu, P.; Ji, J.; Hajra, S.; Chen, J.-X. Free-radical-mediated conjugate additions: Enantioselective synthesis of butyrolactone natural products: (-)-enterolactone, (-)-arctigenin, (-)-isoarctigenin, (-)-nephrosteranic acid, and (-)-roccellaric acid. J. Org. Chem. 2002, 67, 1738-1745;
    • (2002) J. Org. Chem , vol.67 , pp. 1738-1745
    • Sibi, M.P.1    Liu, P.2    Ji, J.3    Hajra, S.4    Chen, J.-X.5
  • 14
    • 0035680770 scopus 로고    scopus 로고
    • Enantioselective syntheses of (+)- and (-)-nephrosteranic acid employing the Nicholas-Schreiber reaction
    • (f) Jacobi, P. A.; Herradura, P. Enantioselective syntheses of (+)- and (-)-nephrosteranic acid employing the Nicholas-Schreiber reaction. Can. J. Chem. 2001, 79, 1727-1735;
    • (2001) Can. J. Chem , vol.79 , pp. 1727-1735
    • Jacobi, P.A.1    Herradura, P.2
  • 15
    • 0029165982 scopus 로고
    • Concise synthesis of natural γ-butyrolactones, (+)-trans-whisky lactone, (+)-trans-cognac lactone, (-)-methylenolactocin, (+)-nephrosteranic acid,(+)-roccellaric acid using novel chiral butenolide synthons
    • (g) Takahata, H.; Uchida, Y.; Momose, T. Concise synthesis of natural γ-butyrolactones, (+)-trans-whisky lactone, (+)-trans-cognac lactone, (-)-methylenolactocin, (+)-nephrosteranic acid,(+)-roccellaric acid using novel chiral butenolide synthons. J. Org. Chem. 1995, 60, 5628-5633;
    • (1995) J. Org. Chem , vol.60 , pp. 5628-5633
    • Takahata, H.1    Uchida, Y.2    Momose, T.3
  • 16
    • 0028319119 scopus 로고
    • New entry to chiral butenolide synthons: Application to expeditious syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-trans-cognac lactone
    • (h) Takahata, H.; Ushida, Y.; Momose, T. New entry to chiral butenolide synthons: Application to expeditious syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-trans-cognac lactone. Tetrahedron Lett. 1994, 35, 4123-4124.
    • (1994) Tetrahedron Lett , vol.35 , pp. 4123-4124
    • Takahata, H.1    Ushida, Y.2    Momose, T.3
  • 17
    • 0034700794 scopus 로고    scopus 로고
    • For roccellaric acid (11) synthesis, see (a) Bella, M.; Margarita, R.; Orlando, C.; Orsini, M.; Parlanti, L.; Piancatelli, G. Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: A short synthesis of (-)-roccellaric acid. Tetrahedron Lett. 2000, 41, 561-566;
    • For roccellaric acid (11) synthesis, see (a) Bella, M.; Margarita, R.; Orlando, C.; Orsini, M.; Parlanti, L.; Piancatelli, G. Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: A short synthesis of (-)-roccellaric acid. Tetrahedron Lett. 2000, 41, 561-566;
  • 18
    • 0029789618 scopus 로고    scopus 로고
    • Efficient stereoselective synthesis of the enantiomers of highly substituted paraconic acid
    • (b) Martin, T.; Rodriguez, C. M.; Martin, V. S. Efficient stereoselective synthesis of the enantiomers of highly substituted paraconic acid. J. Org. Chem. 1996, 61, 6450-6453;
    • (1996) J. Org. Chem , vol.61 , pp. 6450-6453
    • Martin, T.1    Rodriguez, C.M.2    Martin, V.S.3
  • 19
    • 0027466821 scopus 로고
    • First asymmetric synthesis of (+)- and (-)-roccellaric acid and dihydroprotolichesterinic acid
    • (c) Mulzer, J.; Hartl, N. S. First asymmetric synthesis of (+)- and (-)-roccellaric acid and dihydroprotolichesterinic acid. Tetrahedron: Asymmetry 1993, 4, 457-471.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 457-471
    • Mulzer, J.1    Hartl, N.S.2
  • 20
    • 0032478655 scopus 로고    scopus 로고
    • For phaseolinic acid (12) synthesis, see (a) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. Synthesis of (+)- and (-)-phaseolinic acid by combination of enzymatic hydrolysis and chemical transformations with revision of the absolute configuration of the natural product. J. Org. Chem. 1998, 63, 2385-2388;
    • For phaseolinic acid (12) synthesis, see (a) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. Synthesis of (+)- and (-)-phaseolinic acid by combination of enzymatic hydrolysis and chemical transformations with revision of the absolute configuration of the natural product. J. Org. Chem. 1998, 63, 2385-2388;
  • 21
    • 0030580332 scopus 로고    scopus 로고
    • Enantioselective syntheses of (+)- and (-)-phaseolinic acid
    • (b) Jacobi, P. A.; Herradura, P. Enantioselective syntheses of (+)- and (-)-phaseolinic acid. Tetrahedron Lett. 1996, 37, 8297-8300;
    • (1996) Tetrahedron Lett , vol.37 , pp. 8297-8300
    • Jacobi, P.A.1    Herradura, P.2
  • 22
    • 37049091822 scopus 로고
    • Metabolites of the higher fungi, part 22: 2-Butyl-3-methylsuccinic acid and 2-hexylidene-3- methylsuccinic acid from xylariaceous fungi
    • (c) Anderson, J. R.; Edwards, R. L.; Whalley, A. J. S. Metabolites of the higher fungi, part 22: 2-Butyl-3-methylsuccinic acid and 2-hexylidene-3- methylsuccinic acid from xylariaceous fungi. J. Chem. Soc., Perkin Trans. 1, 1985, 1481-1486.
    • (1985) J. Chem. Soc., Perkin Trans. 1 , pp. 1481-1486
    • Anderson, J.R.1    Edwards, R.L.2    Whalley, A.J.S.3
  • 23
    • 85178745824 scopus 로고    scopus 로고
    • For nephromopsinic acid (13) isolation, see (a) Huneck, S.; Takeda, R. Contribution to the chemistry of proto- and allo-protolichesterinic acids. Z. Naturforsch. B 1992, 47, 842-854;
    • For nephromopsinic acid (13) isolation, see (a) Huneck, S.; Takeda, R. Contribution to the chemistry of proto- and allo-protolichesterinic acids. Z. Naturforsch. B 1992, 47, 842-854;
  • 24
    • 15944425751 scopus 로고    scopus 로고
    • Facially controlled c-methylation of oxolanyl and cyclopentyl acetate enolates: Application to the total synthesis of (+)-nephromopsinic acid
    • For synthesis, see
    • (b) For synthesis, see Mulzer, J.; Steffen, U.; Martin, H. J.; Zorn, L. Facially controlled c-methylation of oxolanyl and cyclopentyl acetate enolates: Application to the total synthesis of (+)-nephromopsinic acid. Eur. J. Org. Chem. 2005, 6, 1028-1043;
    • (2005) Eur. J. Org. Chem , vol.6 , pp. 1028-1043
    • Mulzer, J.1    Steffen, U.2    Martin, H.J.3    Zorn, L.4
  • 25
    • 0036943889 scopus 로고    scopus 로고
    • Vicinal dianion of triethyl ethanetricarboxylate: Syntheses of (±)-lichesterinic acid, (±)-phaseolinic acid, (±)-nephromopsinic acid, (±)-roccellaric acid, and (±)-dihydroprotolichesterinic acid
    • (c) Pohmakotr, M.; Harnying, W.; Tuchinda, P.; Reutrakul, V. Vicinal dianion of triethyl ethanetricarboxylate: Syntheses of (±)-lichesterinic acid, (±)-phaseolinic acid, (±)-nephromopsinic acid, (±)-roccellaric acid, and (±)-dihydroprotolichesterinic acid. Helv. Chim. Acta 2002, 85, 3792-3813;
    • (2002) Helv. Chim. Acta , vol.85 , pp. 3792-3813
    • Pohmakotr, M.1    Harnying, W.2    Tuchinda, P.3    Reutrakul, V.4
  • 26
    • 0032563954 scopus 로고    scopus 로고
    • Synthesis of (±)-nephromopsinic acid
    • (d) Forster, A.; Fitremann, J.; Renaud, P. Synthesis of (±)-nephromopsinic acid. Tetrahedron Lett. 1998, 39, 7097-7100;
    • (1998) Tetrahedron Lett , vol.39 , pp. 7097-7100
    • Forster, A.1    Fitremann, J.2    Renaud, P.3
  • 27
    • 0000077973 scopus 로고
    • Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes: Application to the first synthesis of nephromopsinic acid
    • (e) Mulzer, J.; Kattner, L.; Strecker, A. R.; Shroeder, C.; Buschmann, J.; Lehmann, C.; Luger, P. Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes: Application to the first synthesis of nephromopsinic acid. J. Am. Chem. Soc. 1991, 113, 4218-4229.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 4218-4229
    • Mulzer, J.1    Kattner, L.2    Strecker, A.R.3    Shroeder, C.4    Buschmann, J.5    Lehmann, C.6    Luger, P.7
  • 28
    • 0033543463 scopus 로고    scopus 로고
    • For dihydroprotolichesterolic acid (14) synthesis, see (a) Mandal, P. K.; Roy, S. C. Total synthesis of (±)-dihydroprotolichesterinic acid and formal synthesis of (±) -roccellaric acid by radical cyclisation of an epoxide using a transition-metal radical source. Tetrahedron 1999, 55, 11395-11398;
    • For dihydroprotolichesterolic acid (14) synthesis, see (a) Mandal, P. K.; Roy, S. C. Total synthesis of (±)-dihydroprotolichesterinic acid and formal synthesis of (±) -roccellaric acid by radical cyclisation of an epoxide using a transition-metal radical source. Tetrahedron 1999, 55, 11395-11398;
  • 29
    • 0032542162 scopus 로고    scopus 로고
    • Efficient total syntheses of (±)-protolichesterinic acid and (±)-roccellaric acid via tungsten-π-allyl complexes
    • (b) Chen, M. J.; Liu, R. S. Efficient total syntheses of (±)-protolichesterinic acid and (±)-roccellaric acid via tungsten-π-allyl complexes. Tetrahedron Lett. 1998, 39, 9465-9468;
    • (1998) Tetrahedron Lett , vol.39 , pp. 9465-9468
    • Chen, M.J.1    Liu, R.S.2
  • 30
    • 0029002277 scopus 로고
    • A concise synthesis of (-)-dihydroprotolichesterinic acid via consecutive stereocontrolled 1,4-conjugate addition and syn-aldol condensation reactions
    • (c) Banks, M. R.; Dawson, I. M.; Gosney, I.; Hodgson, P. K. G.; Thorburn, P. A concise synthesis of (-)-dihydroprotolichesterinic acid via consecutive stereocontrolled 1,4-conjugate addition and syn-aldol condensation reactions. Tetrahedron Lett. 1995, 36, 3567-3570;
    • (1995) Tetrahedron Lett , vol.36 , pp. 3567-3570
    • Banks, M.R.1    Dawson, I.M.2    Gosney, I.3    Hodgson, P.K.G.4    Thorburn, P.5
  • 31
    • 0000847234 scopus 로고
    • The synthesis of dl- protolichesterinic acid
    • (d) van Tamelen, E. E.; Bach, S. R. The synthesis of dl- protolichesterinic acid. J. Am. Chem. Soc. 1958, 80, 3079-3083.
    • (1958) J. Am. Chem. Soc , vol.80 , pp. 3079-3083
    • van Tamelen, E.E.1    Bach, S.R.2
  • 32
    • 0035799865 scopus 로고    scopus 로고
    • Enantioselective synthesis of (-)-roccellaric acid
    • (a) Boehm, C.; Reiser, O. Enantioselective synthesis of (-)-roccellaric acid. Org. Lett. 2001, 3, 1315-1318.
    • (2001) Org. Lett , vol.3 , pp. 1315-1318
    • Boehm, C.1    Reiser, O.2
  • 33
    • 0001092339 scopus 로고    scopus 로고
    • Huneck, S.; Tonsberg, T.; Bohlmann, F. (-)-Allo-pertusaric acid and (-) -dihydropertusaric acid from the lichen Pertysaria albescens. Phytochemistry 1986, 25, 453-460;
    • (a) Huneck, S.; Tonsberg, T.; Bohlmann, F. (-)-Allo-pertusaric acid and (-) -dihydropertusaric acid from the lichen Pertysaria albescens. Phytochemistry 1986, 25, 453-460;
  • 34
    • 0001037653 scopus 로고
    • Synthetic opportunities offered by anti α-methylene- βhydroxy-γ-alkoxy esters: Stereoselective reactions at the double bond
    • (b) Bernardi, A.; Beretta, M. G.; Colombo, L.; Gennari, C.; Poli, G.; Scolastico, C. Synthetic opportunities offered by anti α-methylene- βhydroxy-γ-alkoxy esters: Stereoselective reactions at the double bond. J. Org. Chem. 1985, 50, 4442-4447;
    • (1985) J. Org. Chem , vol.50 , pp. 4442-4447
    • Bernardi, A.1    Beretta, M.G.2    Colombo, L.3    Gennari, C.4    Poli, G.5    Scolastico, C.6
  • 35
    • 0010370663 scopus 로고
    • Synthesis of dl-lichesterinic acid methyl ester
    • (c) van Tamelen, E. E.; Osborne, C. E.; Bach, S. R. Synthesis of dl-lichesterinic acid methyl ester. J. Am. Chem. Soc. 1955, 77, 4625-4629.
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 4625-4629
    • van Tamelen, E.E.1    Osborne, C.E.2    Bach, S.R.3
  • 36
    • 0000593386 scopus 로고    scopus 로고
    • Predicting the diastereoselectivity of Rh-mediated intramolecular C-H insertion
    • (a) Taber, D. F.; You, K. K.; Rheingold, A. L. Predicting the diastereoselectivity of Rh-mediated intramolecular C-H insertion. J. Am. Chem. Soc. 1996, 118, 547-556;
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 547-556
    • Taber, D.F.1    You, K.K.2    Rheingold, A.L.3
  • 37
    • 84943966860 scopus 로고
    • About the stereospecific α-alkylation of β-hydroxyesters
    • (b) Frater, G. About the stereospecific α-alkylation of β-hydroxyesters. Helv. Chim. Acta 1979, 62, 2825-2828.
    • (1979) Helv. Chim. Acta , vol.62 , pp. 2825-2828
    • Frater, G.1
  • 38
    • 0141518570 scopus 로고    scopus 로고
    • Unusual, strained heterocycles: 3-Alkylidene-2-methyleneoxetanes from Morita-Baylis-Hillman-type adducts
    • Martinez, I.; Andrews, A. E.; Emch, J. D.; Ndalaka, A. J.; Wang, J.; Howell, A. R. Unusual, strained heterocycles: 3-Alkylidene-2-methyleneoxetanes from Morita-Baylis-Hillman-type adducts. Org. Lett. 2003, 5, 399-402.
    • (2003) Org. Lett , vol.5 , pp. 399-402
    • Martinez, I.1    Andrews, A.E.2    Emch, J.D.3    Ndalaka, A.J.4    Wang, J.5    Howell, A.R.6
  • 39
    • 0029131728 scopus 로고
    • Synthesis of an analog of biosynthetic precursor Ia of lipid A by an improved method: A novel antagonist containing four (S)-3-hydroxy fatty acid
    • (a) Fukase, K.; Liu, W. C.; Suda, Y.; Oikawa, M.; Wada, A.; Mori, S.; Ulmer, A. J.; Rietschel, E. T.; Kusumoto, S. Synthesis of an analog of biosynthetic precursor Ia of lipid A by an improved method: A novel antagonist containing four (S)-3-hydroxy fatty acid. Tetrahedron Lett. 1995, 36, 7455-7458;
    • (1995) Tetrahedron Lett , vol.36 , pp. 7455-7458
    • Fukase, K.1    Liu, W.C.2    Suda, Y.3    Oikawa, M.4    Wada, A.5    Mori, S.6    Ulmer, A.J.7    Rietschel, E.T.8    Kusumoto, S.9
  • 40
    • 0027157208 scopus 로고
    • Towards the chemoenzymatic synthesis of lipid A
    • (b) Sugai, T.; Ritzen, H.; Wong, C. H. Towards the chemoenzymatic synthesis of lipid A. Tetrahedron: Asymmetry 1993, 4, 1051-1058;
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1051-1058
    • Sugai, T.1    Ritzen, H.2    Wong, C.H.3
  • 41
    • 0001222554 scopus 로고
    • Asymmetric reduction of aliphatic short to long chain β keto acid by use of fermenting baker's yeast
    • (c) Utaka, M.; Watabu, H.; Higashi, H.; Sakai, T.; Tsuboi, S.; Torii, S. Asymmetric reduction of aliphatic short to long chain β keto acid by use of fermenting baker's yeast. J. Org. Chem. 1990, 55, 3917-3921.
    • (1990) J. Org. Chem , vol.55 , pp. 3917-3921
    • Utaka, M.1    Watabu, H.2    Higashi, H.3    Sakai, T.4    Tsuboi, S.5    Torii, S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.