本文へスキップ

南雲研究室 Synthetic Organic Chemistry

発表論文HEADLINE


 2014 2013 2012 2011 2010 2009~2005 2004~2000 1999~1995 1994~1988
2016
Selective Mono-reduction of Pyrrole-2,5 and 2,4-Dicarboxylates.

Eiko Yasui, Jyunpei Tsuda, Satoshi Ohnuki, Shinji Nagumo
Chem. Pharm. Bull. 2016, 64(9), 1262-1267.

2015
Synthetic study of arenicolide C: stereoselective synthesis of the C19–C36 segment.
Sho Sunagawa, Haruki Yamada, Minako Naito, Eiko Yasui, Megumi Mizukami, Masaaki Miyashita, Shinji Nagumo.
Tetrahedron Lett. 2015, 56(48), 6693-6695.

2014

Ring opening of disubstituted epoxides linked to a secondary oxygen group with an organocopper reagent.
Naoki Terayama, Shodai Ushijima, Eiko Yasui, Masaaki Miyashita, Shinji Nagumo.
Tetrahedron Lett. 2014, 55(48), 6515-6519.

Total Synthesis and structural revision of Sekothrixide.
Naoki Terayama, Eiko Yasui, Megumi Mizukami, Masaaki Miyashita, Shinji Nagumo.
Org. Lett. 2014, 16(11), 2794-2797.

Synthesis of 1-(4-Aminobutyl)-2-iminoimidazolidin-4-one Aimed at Preparation of a Creatinine-Specific Antibody.
Shun-suke Moriya, Naoki Terayama, Kyoko Hiramatsu, Masao Kawakita, Tatsuya Kiryu, Takato Kawanishi, Eiko Yasui, Shinji Nagumo.
Chem. Pharm. Bull. 2014, 62(4), 350-353.

Synthesis and Evaluation of a Cyclopropane Derivative of DHMEQ.
Eiko Yasui, Kan Takayama, Takahiro Nakago, Nobuyuki Takeda, Yasutada Imamura, Shinji Nagumo.
Chem. Pharm. Bull. 2014, 62(3), 304-307.

2013

A novel method for the synthesis of 3,4-disubstitutedpyrrole-2,5-dicarboxylates from hydrazones derived from a-diazo esters.
Yasui, E.; Wada, M.; Nagumo, S.; Takamura, N.
Tetrahedron 2013, 69(21), 4325-4330.


Novel method for construction of tetrahydro-1-benzazepine and tetrahydro-2-benzazepine based on 7-endo selective Friedel–Crafts cyclization of vinyloxirane.
Mizukami, M.; Wada, K.; Sato, G.; Ishii, Y.; Kawahara, N.; Nagumo, S.
Tetrahedron 2013, 69(20), 4120-4138.

2012年

Tandem five membered-ring selective Prins reaction and Friedel-Crafts reaction.
Suzuki, Y.; Niwa, T.; Yasui, E.; Mizukami, M.; Miyashita, M.; Nagumo, S.
Tetrahedron Lett. 2012, 53(11), 1337-1340.


2011年

Synthetic studies of venturicidins: stereoselective synthesis of the C15-C27 segment based on two types of stereospecific epoxide opening reactions
Suzuki, Y.; Nagumo, S.; Yasui, E.; Mizukami, M.; Miyashita, M.
Tetrahedron Lett. 2011, 52(51), 6948-6951.



Synthetic studies of the Lichen macrolide lepranthin. Stereoselective synthesis of the diolide framework based on regioselective epoxide-opening reactions.
Takada, H.; Nagumo, S.; Yasui, E.; Mizukami, M.; Miyashita, M.
Chem. Pharm. Bull. 2011, 59(4), 525-527.


Friedel-Crafts reaction of vinylaziridine linked to an ester group.
Takada, H.; Yasui, E.; Sahara, Y.; Chinen, Y.; Tanaka, H.; Morita, Y.; Kobiki, C.; Narisawa, D.; Mizukami, M.; Miyashita, M.; Nagumo, S.
Heterocycles, 2011, 83(3), 555-570.



Synthetic studies of lepranthin, a lichen-produced dimeric macrolide. Stereoselective synthesis of a seco-acid based on stereospecific epoxide-opening reactions.
Takada, H.; Nagumo, S.; Yasui, E.; Mizukami, M.; Miyashita, M.
Heterocycles, 2011, 83(2), 293-298.


2010年

Stereoselective Synthesis of the C25-C36 Segment of Arenicolides A and B: Determination of the Configuration of the trisubstituted Epoxide.
Nagumo, S.; Nakano, T.; Hata, K.; Mizukami, M.; Miyashita, M.
Organic Lett. 2010, 12(5), 908-911.


2009~2005

Intramolecular Friedel-Crafts type reaction of vinyloxiranes linked to an ester group.
Nagumo, S.; Miura, T.; Mizukami, M.; Miyoshi, I.; Imai, M.; Kawahara, N.; Akita, H.
Tetrahedron 2009, 65(47), 9884-9896.



8-Endo selective Friedel-Crafts cyclization of vinyloxiranes with Co2(CO)6-complexed acetylene.
Nagumo, S.; Ishii, Y.; Sato, G.; Mizukami, M.; Imai, M.; Kawahara, N.; Akita, H.
Tetrahedron Lett. 2009, 50(1), 26-28.


Novel construction of hydro-2-benzazepines based on 7-endo selective Friedel-Crafts-type reaction of vinyloxirane.
Nagumo, S.; Mizukami, M.; Wada, K.; Miura, T.; Bando, H.; Kawahara, N.; Hashimoto, Y.; Miyashita, M.; Akita, H.
Tetrahedron Lett. 2007, 48(48), 8558-8561.


Facile synthesis of medium-sized cyclic amines based on Friedel-Crafts reaction via iminium cation by use of acetylene dicobalt complex.
Mizukami, M.; Saito, H.; Higuchi, T.; Imai, M.; Bando, H.; Kawahara, N.; Nagumo, S.
Tetrahedron Lett. 2007, 48(40), 7228-7231.



Nitrile-Promoted Rh-Catalyzed Intermolecular Hydroacylation of Olefins with Salicylaldehyde.
Imai, M.; Tanaka, M.; Nagumo, S.; Kawahara, N.; Suemune, H.
J. Org. Chem. 2007, 72(7), 2543-2546.


Synthetic study of tautomycin. Part 2: synthesis of Ichihara's fragment based on regioselective enzymatic acetylation of complex molecule.
Ishii, Y.; Nagumo, S.; Arai, T.; Akuzawa, M.; Kawahara, N.; Akita, H.
Tetrahedron 2006, 62(4), 716-725.


2004~2000

Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation between Salicylaldehydes and 1,4-Penta- or 1,5-Hexadienes.
Imai, M.; Tanaka, M.; Tanaka, K.; Yamamoto, Y.; Imai-Ogata, N.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H.
J. Org. Chem. 2004, 69(4), 1144-1150.



Stereoselective syntheses of 2,5-disubstituted hydroxyfuran derivatives as synthon of polyether antibiotics.
Nagumo, S.; Ishii, Y.; Kanno, S.; Kawahara, N.
Heterocycles 2003, 59(2), 859.


Double-Chelation-Assisted Rh-Catalyzed Intermolecular Hydroacylation.
Tanaka, M.; Imai, M.; Yamamoto, Y.; Tanaka, K.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H.
Org. Lett. 2003, 5(8), 1365-1367.



Stereoselective syntheses of 2,5-disubstituted hydroxyfuran derivatives as synthon of polyether antibiotics.
Nagumo, S.; Ishii, Y.; Kanno, S.; Kawahara, N.
Heterocycles 2003, 59(1), 101-105.


Synthesis of (-)-TAN1251A using 4-hydroxy-l-proline as a chiral source.
Nagumo, S.; Matoba, A.; Ishii, Y.; Yamaguchi, S.; Akutsu, N.; Nishijima, H.; Nishida, A.; Kawahara, N.
Tetrahedron 2002, 58(49), 9871-9877.


Intramolecular Reaction of a Phenonium Ion. Novel Lactonization of 4-Aryl-5-tosyloxypentanoates and 4-Aryl-5-tosyloxyhexanoates Concomitant with a Phenyl Rearrangement.
Nagumo, S.; Ono, M.; Kakimoto, Y.; Furukawa, T.; Hisano, T.; Mizukami, M.; Kawahara, N.; Akita, H.
J. Org. Chem. 2002, 67(19), 6618-6622.


Novel ether-ring transformation via a phenonium ion.
Nagumo, S.; Ishii, Y.; Kakimoto, Y.; Kawahara, N.
Tetrahedron Lett. 2002, 43(30), 5333-5337.


Total synthesis of antimuscarinic alkaloid, (±)-TAN1251A.
Nagumo, S.; Nishida, A.; Yamazaki, C.; Matoba, A.; Murashige, K.; Kawahara, N.
Tetrahedron 2002, 58(24), 4917-4924.



Novel skeletal rearrangement of hydroindan derivatives into hydroazulenones via an alkoxy radical.
Goto, M.; Miyoshi, I.; Ishii, Y.; Ogasawara, Y.; Kakimoto, Y.; Nagumo, S.; Nishida, A.; Kawahara, N.; Nishida, M.
Tetrahedron 2002, 58(12), 2339-2350.


7-endo Selective Friedel-Crafts type cyclization of vinyloxiranes linked to an ester group.
Nagumo, S.; Miyoshi, I.; Akita, H.; Kawahara, N.
Tetrahedron Lett. 2002, 43(12), 2223-2226.


1999~1995

The synthetic studies of novel alkaloid, TAN1251 A.
Nagumo, S.; Akutsu, N.; Yamazaki, C.; Kawahara, N.; Nishida, A.
Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1998, 40th, 595-600.


Alkylation of 4-hydroxyproline ester derivatives. Diastereoselectivity guided by the anomeric effect and π-interaction.
Nagumo, S.; Mizukami, M.; Akutsu, N.; Nishida, A.; Kawahara, N.
Tetrahedron Lett. 1999, 40(16), 3209-3212.



Lactonization of methyl 4-aryl-5-(tosyloxy)hexanoates via a phenonium ion.
Nagumo, S.; Hisano, T.; Kakimoto, Y.; Kawahara, N.; Ono, M.; Furukawa, T.; Takeda, S.; Akita, H.
Tetrahedron Lett. 1998, 39(44), 8109-8112.



Total synthesis of (±)-TAN 1251A.
Nagumo, S.; Nishida, A.; Yamazaki, C.; Murashige, K.; Nawahara, N.
Tetrahedron Lett. 1998, 39(25), 4493-4496.



Novel lactonization induced by the phenonium ion.
Nagumo, S.; Furukawa, T.; Ono, M.; Akita, H.
Tetrahedron Lett. 1997, 38(16), 2849-2852.


A synthesis of (2R,4'R,8'R)-α-tocopherol (vitamin E) side chain.
Chen, C. Y.; Nagumo, S.; Akita, H.
Chem. Pharm. Bull. 1996, 44(11), 2153-2156.



Enzymic hydrolysis of meso(syn-syn)-1,3,5-triacetoxy-2,4-dimethylpentane and acetylation of meso(syn-syn)-3-benzyloxy-2,4-dimethylpentane-1,5-diol by lipase.
Nagumo, S.; Arai, T.; Akita, H.
Chem. Pharm. Bull. 1996, 44(7), 1391-1394.


A formal total synthesis of xanthorrhizol based on nucleophilic opening of vinyloxirane by arylcopper reagent.
Nagumo, S.; Irie, S.; Hayashi, K.; Akita, H.
Heterocycles 1996, 43(6), 1175-1178.


Reaction of methyl 4,5-epoxy-(2E)-pentenoate with arylcopper reagents.
Nagumo, S.; Irie, S.; Akita, H.
Chem. Pharm. Bull. 1996, 44(4), 675-80.


The reaction of methyl (E)-4,5-epoxypent-2-enoate with arylcopper: the unique role of boron trifluoride in determining regioselectivity.
Nagumo, S.; Irie, S.; Akita, H.
Chem. Comm. 1995, (19), 2001-2.


Formal total syntheses of (-)-oudemansins A, B and X based on a lipase-catalyzed hydrolysis of an acetate.
Akita, H.; Chen, C. Y.; Nagumo, S.
J. Chem. Soc. Perkin Trans. 1: Org. bioorg. Chem. 1995, (17), 2159-64.



Total synthesis of (±)-, (-)-, and (+)-oudemansin X.
Umezawa, I.; Nozawa, M.; Nagumo, S.; Akita, H.
Chem. Pharm. Bull. 1995, 43(7), 1111-18.

1994~1988


A highly stereoselective synthesis of chiral synthon based on enzymic function and its application to the synthesis of natural products.
Chen, C. Y.; Nagumo, S.; Umezawa, I.; Ono, M.; Akita, H.
Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1994, 36th, 549-56.



Lipase catalyzed resolution of (±)-2-substituted 1-propanol derivatives possessing an aromatic ring.
Akita, H.; Nozawa, M.; Umezawa, I.; Nagumo, S.
Biocatalysis 1994, 9(1-4), 79-87.


Formal synthesis of N-trifluoroacetyl-L-acosamine and N-trifluoroacetyl-L-daunosamine from an achiral precursor, methyl sorbate.
Nagumo, S.; Umezawa, I.; Akiyama, J.; Akita, H.
Chem. Pharm. Bull. 1995, 43(1), 171-3.



Catalytic properties of carbonyl reductase from rabbit kidney for acetohexamide and its analogs. Imamura, Y.; Higuchi, T.; Otagiri, M.; Nagumo, S.; Akita, H.
Bioorg. Chem. 1994, 22(4), 387-94.



Synthesis of ozonolysis products of myxothiazol.
Akita, H.; Nozawa, M.; Nagumo, S.
Chem. Pharm. Bull. 1994, 42(6), 1208-12.


Catalytic properties of carbonyl reductase from rabbit liver for analogs of acetohexamide and 4-acetylpyridine.
Imamura, Y.; Koga, T.; Higuchi, T.; Otagiri, M.; Sugino, E.; Hibino, S.; Nagumo, S.; Akita, H.
Biochemistry and Molecular Biology International 1994, 33(5), 893-9.



A highly stereoselective synthesis of the versatile chiral synthons possessing two stereogenic centers, the formal total syntheses of (-)-oudemansins A, B, and X.
Akita, H.; Chen, C. Y.; Nagumo, S.
Tetrahedron: Asymmetry 1994, 5(7), 1207-10.


Novel ring cleavage based on intermolecular aldol condensation.
Nagumo, S.; Matsukuma, A.; Suemune, H.; Sakai, K.
Tetrahedron 1993, 49(46), 10501-10.


Total synthesis of (-)-oudemansin X based on enzymic resolution using immobilized lipase.
Akita, H.; Umezawa, I.; Nozawa, M.; Nagumo, S.
Tetrahedron: Asymmetry 1993, 4(5), 757-60.


Synthesis of (R)-(-)-phoracantholide I based on stereocontrolled cleavage of internal acetal.
Nagumo, S.; Suemune, H.; Sakai, K.
Tetrahedron 1992, 48(40), 8667-76.


Drastic ring transformation reactions of fused bicyclic rings to bridged bicyclic rings.
Yamamoto, T.; Eki, T.; Nagumo, S.; Suemune, H.; Sakai, K.
Tetrahedron 1992, 48(22), 4517-24.


Preparation of chiral straight-chain compounds with syndiotactic methyl function.
Matsukuma, A.; Nagumo, S.; Suemune, H.; Sakai, K.
Tetrahedron Lett. 1991, 32(51), 7559-62.



Synthesis of phoracantholide I based on stereospecific fragmentation reactions.
Nagumo, S.; Suemune, H.; Sakai, K.
Tetrahedron Lett. 1991, 32(40), 5585-8.


Novel skeletal transformation of bicyclo[3.3.0]octanones to bicyclo[3.2.1]octenes.
Yamamoto, T.; Eki, T.; Nagumo, S.; Suemune, H.; Sakai, K.
Tetrahedron Lett. 1991, 32(4), 515-16.


Stereocontrolled synthesis of (±)-acorenone B based on new ring conversion.
Nagumo, S.; Suemune, H.; Sakai, K.
Chem. Comm. 1990, (24), 1778-9.


Ring cleavage reaction based on intermolecular aldol condensation.
Nagumo, S.; Matsukuma, A.; Inoue, F.; Yamamoto, T.; Suemune, H.; Sakai, K.
Chem. Comm. 1990, (21), 1538-9.


Drastic conversion of bicyclo[m.n.0]alkane rings to spirocyclic skeletons.
Nagumo, S.; Suemune, H.; Sakai, K.
Tetrahedron Lett. 1988, 29(52), 6927-30.


工学院大学有機合成化学研究室

〒192-0015
東京都八王子市中野町2665-1

TEL 042-628-4870