岡山大学 工学部 化学生命系学科/大学院自然科学研究科 応用化学専攻

生物有機化学研究室
坂倉研究室/SAKAKURA Group



更新日: 2017-12-08

溝口玄樹助教が着任しました

12月1日付で溝口玄樹助教が着任しました。
(2017.12.1)

学会発表

「ガタスタチンをリード化合物としたγ-チューブリン特異的阻害剤の開発研究 」
早川一郎,畑中大成, 塩田秀也,知念拓実,恵比寿春菜,臼井健郎,木越英夫,坂倉彰
第35回メディシナルケミストリーシンポジウム,ポスター発表,名古屋大学豊田講堂,10月25日〜27日,1P-083
(2017.10.27)

論文発表

Regioselective DMAD-insertion Reaction of Silyl Dienol Ether of γ-Pyrone under Catalyst- and Heating-Free Conditions
Ichiro Hayakawa,* Yuji Yamanaka, Koichi Mitsudo, Hiromi Ota, and Akira Sakakura*
Heterocycles 2017, 94 (12), 2299–2306.
DOI: 10.3987/COM-17-13820
GA-DMAD.png
The reaction of silyl dienol ether of γ-pyrone with dimethyl acetylenedicarboxylate (DMAD) gives the regioselective insertion product in 66% yield. This DMAD-insertion reaction is thought to include a three-step sequence: (1) thermal [2+2]-type cycloaddition reaction of silyl dienol ether of γ-pyrone with DMAD, (2) ring-opening electrocyclic reaction of the cyclobutene skeleton, and (3) hydrolysis of the silyl dienol ether. The present reaction proceeds under mild conditions without any catalysts or heating. In addition, the [2+2]-type cycloaddition reaction proceeds regioselectively at the C3–C4 double bond in the silyl dienol ether of γ-pyrone.
(2017.10.26)

論文発表

Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen-Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C
Takayuki Kudoh, Yuya Araki, Natsumi Miyoshi, Mizuho Tanioka, and Akira Sakakura*
Asian J. Org. Chem. 2017, in press.
DOI: 10.1002/ajoc.201700568
GA-manzacidin.png
β,β-Disubstituted β-amino alcohols has been synthesized in a diastereodivergent manner from chiral secondary nitroalkanes as starting materials. In this key Henry reaction, the use of different protecting groups resulted in the diastereoselective construction of the tetrasubstituted carbon stereocenter with different configuration. Based on this methodology, a total synthesis of manzacidins A and C has been achieved.
(2017.10.19)

研究室旅行 香川,愛媛の旅

9/25:讃岐うどん打ち体験,金刀比羅宮,道後温泉
9/26:松山城,今治タオル美術館,マイントピア別子銅山
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(2017.9.26)

学会発表

ユズリハアルカロイド・ユズリミン類の合成研究
早川一郎,池田将規,新井田恵介,中重雄一,永易杏菜,野村紗希,齊藤啓太,木越英夫,坂倉彰
第59回天然有機化合物討論会,ポスター発表,わくわくホリデーホール(札幌市民ホール),9月20日〜22日,P-33
(2017.9.22)

講演会

シストセンチュウふ化促進物質の不斉全合成
谷野 圭持 教授(北海道大学大学院理学研究院)
2017年9月14日
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(2017.9.15)

集中講義

谷野 圭持 教授(北海道大学大学院理学研究院)
2017年9月14日,15日
(2017.9.15)

学会発表

ルイス酸およびブレンステッド酸触媒を用いる不飽和2級アルコールの分子内ハロエーテル環化反応の検討
塩本啓一,坂倉彰
第33回若手化学者のための化学道場,ポスター発表,鳥取県鳥取市 レーク大樹,2017年9月1日,2日

キラル有機アンモニウム塩触媒を用いたニトロンとα-アシロキシアクロレインとのエナンチオ選択的1,3-双極子環化付加反応の開発
鬼童ちひろ,坂倉彰
第33回若手化学者のための化学道場,ポスター発表,鳥取県鳥取市 レーク大樹,2017年9月1日,2日
(2017.9.2)

論文発表

Heat Versus Basic Conditions: Intramolecular Dehydro-Diels–Alder Reaction of 1-Indolyl-1,6-heptadiynes for the Selective Synthesis of Substituted Carbazoles
Takayuki Kudoh, Syo Fujisawa, Megumi Kitamura, Akira Sakakura*
Synlett 2017, 28, 2189–2193.
DOI: 10.1055/s-0036-1588461
GA-carbazole.png
The intramolecular dehydro-Diels–Alder reaction of 1-indolyl-1,6-heptadiynes proceeds smoothly under rather mild heating conditions to give substituted carbazoles in moderate to good yields. The reaction of 7-aryl-1-indolyl-1,6-heptadiynes under heating gives the corresponding carbazoles chemoselectively in high yields, whereas the reaction under basic conditions gives naphthalenes as major products.
(2017.7.6)

招待講演

"Biomimetic Cyclization of 3,5-Diketoesters: Application to Total Synthesis of Cyercene A, an α-Methoxy-γ-Pyrone-Containing Polypropionate"
Akira Sakakura
International Symposium on Pure & Applied Chemistry (ISPAC) 2017
Hotel Continental Saigon, Ho Chi Minh City, Vietnam, June 8–10, 2017
Oral Presentation, ORG42
(2017.6.10)

学会発表

"Total Synthesis of Manzacidins A and C Based on Diastereoselective Hydroxymethylation of Chiral Nitroalkanes"
Yuya Araki, Mizuho Tanioka, Natsumi Miyoshi, Takayuki Kudoh, Akira Sakakura
International Symposium on Pure & Applied Chemistry (ISPAC) 2017
Hotel Continental Saigon, Ho Chi Minh City, Vietnam, June 8–10, 2017
Oral Presentation, ORG67
(2017.6.10)

論文発表

Reinvestigation of the Biomimetic Cyclization of 3,5-Diketoesters: Application to the Total Synthesis of Cyercene A, an α-Methoxy-γ-Pyrone-Containing Polypropionate
Kai Onda, Ichiro Hayakawa, Akira Sakakura*
Synlett 2017, 28 (13), 1596–1600.
DOI: 10.1055/s-0036-1588795
GA-gamma-pyrone.png
The biomimetic cyclization of 3,5-diketoesters was reinvestigated for the synthesis of α-methoxy-γ-pyrones. 3,5-Diketoesters were selectively synthesized via the aldol reaction of commercially available methyl 2-methyl-3-oxopentanoate with an aldehyde followed by the oxidation with AZADOL® and PhI(OAc)2. The DBU-promoted intramolecular transesterification of 3,5-diketoesters showed excellent reactivity in MeOH, to give the corresponding γ-hydroxy-α-pyrones in high yields under mild reaction conditions. Based on the present cyclization scheme, the total synthesis of cyercene A was achieved.
(2017.4.26)

2017年度始動

M2 6人,M1 3人,B4 10人とともに,2017年度がスタートしました。
(2017.4.3)

当研究室では,複雑な骨格や多彩な官能基を持つ生物活性物質の全合成や,有機触媒を利用した不斉合成法の開発に取り組んでいます。