Papers - Sugai, Takeshi

Formal synthesis of englerin A utilizing regio- and diastereoselective [4 + 3] cycloaddition

S. Hagihara, K. Hanaya, T. Sugai, M. Shoji

J. Antibiot. (Journal of Antibiotics)  71 ( 2 ) 257 - 262 2018.02

Research paper (scientific journal), Joint Work, Accepted,  ISSN  00218820

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© 2018 Japan Antibiotics Research Association All rights reserved. Englerin A, a guaiane sesquiterpene isolated from Phyllanthus engleri, showed highly potent and selective growth inhibitory activities against renal cancer cell lines. We synthesized the key tricyclic intermediate from commercially available 2,2-dimethyl-1,3-dioxan-5-one via regio- and diastereoselective [4+3] cycloaddition between the formyl enol silyl ether and the disubstituted furan, in 4.8% total yield over 10 steps.

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Synthesis of fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation

Tsunekawa R., Hanaya K., Higashibayashi S., Sugai T.

Bioscience, Biotechnology and Biochemistry (Bioscience, Biotechnology and Biochemistry)  82 ( 8 ) 1316 - 1322 2018

ISSN  09168451

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© 2018 Japan society for Bioscience, Biotechnology, and Agrochemistry. Fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.

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Chemoenzymatic approaches to the synthesis of the (1S,2R)-isomer of benzyl 2-hydroxycyclohexanecarboxylate

R. Tsunekawa, K. Hanaya, S. Higashibayashi, M. Shoji, T. Sugai

Mol. Catal. (Molecular Catalysis)  444   84 - 89 2017.11

Research paper (scientific journal), Joint Work, Accepted,  ISSN  24688231

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© 2017 Elsevier B.V. We examined ten strains of cultured whole-cell yeasts for the asymmetric reduction of commercially available ethyl 2-oxocyclohexanecarboxylate, and found that the (1S,2S)-stereoisomer of ethyl 2-hydroxycyclohexanecarboxylate was the major stereoisomer produced by Williopsis californica JCM 3600. The ethyl group of the ester was then substituted with a benzyl group with low volatility and increased hydrophobicity to facilitate the isolation of the expected product. Incubation with W. californica furnished benzyl (1S,2S)-2-hydroxycyclohexanecarboxylate (>99.9% ee) in 51.0% yield together with its (1R,2S)-isomer (>99.9% ee) in 35.4% yield. Upon treatment of the same substrate bearing the benzyl ester with a screening kit of purified overexpressed carbonyl reductases (Daicel Chiralscreen® OH), two enzymes (E031, E078) furnished the (1R,2S)-isomer as the major product. With another enzyme (E007), the (1S,2R)-isomer was obtained, but its ee was very low (25.6%). The highly enantiomerically enriched (1S,2S)-isomer obtained by W. californica was transformed to the (1S,2R)-isomer (>99.9% ee), whose availability until now has been low, in 43.3% yield over two steps involving tosylation and subsequent inversive attack with tetrabutylammonium nitrite.

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Construction of 2,6,9,11-tetraoxatricyclo[6.2.1.03,8]undecane containing 4-keto-D-glucose skeleton

B. Fujitani, K. Hanaya, S. Higashibayashi, M. Shoji, T. Sugai

Tetrahedron 73   7217 - 7222 2017.11

Research paper (scientific journal), Joint Work, Accepted

A novel phenylphthalimide derivative, pegylated TC11, improves pharmacokinetic properties and induces apoptosis of high-risk myeloma cells via G2/M cell-cycle arrest

S. Aida, M. Hozumi, D. Ichikawa, K. Iida, Y. Yonemura, N. Tabata, T. Yamada, M. Matsushita, T. Sugai, H. Yanagawa, Y. Hattori

Biochem. Biophys. Res. Commun. 493   514 - 520 2017.11

Research paper (scientific journal), Joint Work, Accepted

Synthesis of the 1,2-seco fusicoccane diterpene skeleton by Stille coupling reaction between the highly functionalized A and C ring segments of cotylenin A

K. Kuwata, K. Hanaya, S. Higashibayashi, T. Sugai, M. Shoji

Tetrahedron 73   6039 - 6045 2017.09

Research paper (scientific journal), Joint Work, Accepted

Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation

Y. Yamashita, A. Biard, K. Hanaya, M. Shoji, T. Sugai

Biosci. Biotechnol. Biochem. 65   1279 - 1284 2017.07

Research paper (scientific journal), Joint Work, Accepted

Chemo-enzymatic synthesis of (R)-5-hydroxymethyl-2-isopropyl-5-methylcyclopente-1-yl trifluoromethylsulfonate, a potential chiral building block for multicyclic terpenoid

K. Kuwata, K. Hanaya, T. Sugai, M. Shoji

Tetrahedron: Asymmetry 28   964 - 968 2017.05

Research paper (scientific journal), Joint Work, Accepted

Synthesis of trans,trans,cis-fused tetracyclic skeleton via radical domino cyclization

M. Furuta, K. Hanaya, T. Sugai, M. Shoji

Tetrahedron 73   2316 - 2322 2017.03

Research paper (scientific journal), Joint Work, Accepted

Synthesis of linezolid metabolites PNU-142300 and PNU-142586 toward the exploration of metabolite-related events

K. Hanaya, K. Matsumoto, Y. Yokoyama, J. Kizu, M. Shoji, T. Sugai

Chem. Pharm. Bull. 65   194-199 2017.02

Research paper (scientific journal), Joint Work, Accepted

Synthesis of benzyl tetra-O-acetyl-α-L-glucopyranoside from benzyl 2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

H. Okazaki, Y. Ueda, K. Hanaya, M. Shoji, T. Sugai

Heterocycles 95   862 - 871 2016.11

Research paper (scientific journal), Joint Work, Accepted

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Preparation of (R)-3-hydroxy-N-methylpiperidine, a synthetic key intermediate of (R)-mepenzolate, based on the lipase-catalyzed resolution of the racemic form

Y. Yamashita, K. Hanaya, M. Shoji, and T. Sugai

Heterocycles 95   370 - 379 2016.10

Research paper (scientific journal), Joint Work, Accepted

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Simple Synthesis of Sakuranetin and Selinone via a Common Intermediate, Utilizing Complementary Regioselectivity in the Deacetylation of Naringenin Triacetate

Y. Yamashita, K. Hanaya, M. Shoji, and T. Sugai

Chem. Pharm. Bull. 64   961-965 2016.08

Research paper (scientific journal), Joint Work, Accepted

Ex Situ Enantioconvergent Approaches for the Effective Use of Undesired Isomers: Stereochemical Convergence of a Substrate with Multiple Chiral Centers and Recycling of a Decarboxylated Byproduct

Y. Yamashita, T. Kurihara, T. Horiguchi, A. Miki, M. Shoji, T. Sugai, and K. Hanaya

Synthesis 48   2191-2200 2016.04

Research paper (scientific journal), Joint Work, Accepted

Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene

K. Fukaya, Y. Yamaguchi, A. Watanabe, H. Yamamoto, T. Sugai, T. Sugai, T. Sato, and N. Chida

J. Antibiot. 69   273-279 2016.02

Research paper (scientific journal), Joint Work, Accepted

Development of a Novel Sulfonate Ester-Based Prodrug Strategy

K. Hanaya, S. Yoshioka, S. Ariyasu, S. Aoki, M. Shoji, T. Sugai

Bioorg. Med. Chem. Lett 26   545-550 2016.01

Research paper (scientific journal), Joint Work, Accepted

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Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranosideusing lipase-catalyzed regioselective deacetylation of polyphenolglycoside peracetates as the key step

S. Hanamura, K. Hanaya, M. Shoji, and T. Sugai

J. Mol. Catal. B: Enz. 128   19-26 2016.01

Research paper (scientific journal), Joint Work, Accepted

New Synthesis of Artepillin C, a Prenylated Phenol, Utilizing Lipase-catalyzed Regioselective Deacetylation as the Key Step

K. Yashiro, K. Hanaya, M. Shoji, T. Sugai

Biosci. Biotechnol. Biochem. 26   1926-1930 2015.11

Research paper (scientific journal), Joint Work, Accepted

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Recognition of the remote chiral center in lipase-catalyzed kinetic resolution of [2-methyl-2-(2′-naphthyl)-1,3-benzodioxol-4-yl]methyl acetate, the precursor of 2-methyl-2-(2′-naphthyl)-1,3-benzodioxole-4-carboxylic acid (MNB carboxylic acid)

N. Natori, K. Nakagawara, M. Shoji, T. Sugai and K. Hanaya

J. Mol. Catal. B: Enz. 109   130-135 2014.10

Research paper (scientific journal), Joint Work, Accepted

Synthesis and biological comparison of enantiomers of mepenzolate bromide, a muscarinic receptor antagonist with bronchodilatory and anti-inflammatory activities

Y. Yamashita, K. Tanaka, T. Asano, N. Yamakawa, D. Kobayashi, T. Ishihara, K. Hanaya, M. Shoji, T. Sugai, M. Wada, T. Mashimo, Y. Fukunishi and T. Mizushima

Bioorg. Med. Chem. 22   3488-3497 2014.06

Research paper (scientific journal), Joint Work, Accepted