Literature DB >> 22971928

Organocatalytic asymmetric syntheses of inthomycins A, B and C.

Madoka Yoshino1, Kohei Eto, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama.   

Abstract

The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (-)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1-C7 (iododienyl)aldol units by taking advantage of a Cinchona alkaloid-catalyzed asymmetric β-lactone synthesis and their isomerisation-free Stille coupling with (E)-5-(3-(tributylstannyl)allyl)oxazole.

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Year:  2012        PMID： 22971928     DOI： 10.1039/c2ob26084k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  8 in total

1.  Production and Identification of Inthomycin B Produced by a Deep-Sea Sediment-Derived Streptomyces sp. YB104 Based on Cultivation-Dependent Approach.

Authors:  Qihao Wu; Gaiyun Zhang; Bixia Wang; Xin Li; Shaopeng Yue; Jianwei Chen; Huawei Zhang; Hong Wang
Journal:  Curr Microbiol       Date:  2018-03-08       Impact factor: 2.188

Review 2.  The oxazolomycin family: a review of current knowledge.

Authors:  Patrik Oleksak; Jozef Gonda; Eugenie Nepovimova; Kamil Kuca; Kamil Musilek
Journal:  RSC Adv       Date:  2020-11-09       Impact factor: 4.036

3.  Stereoselective synthesis of dienyl-carboxylate building blocks: formal synthesis of inthomycin C.

Authors:  Caroline Souris; Frédéric Frébault; Ashay Patel; Davide Audisio; K N Houk; Nuno Maulide
Journal:  Org Lett       Date:  2013-06-13       Impact factor: 6.005

Review 4.  Progress in the total synthesis of inthomycins.

Authors:  Bidyut Kumar Senapati
Journal:  Beilstein J Org Chem       Date:  2021-01-07       Impact factor: 2.883

5.  Oxazolomycins produced by Streptomyces glaucus and their cytotoxic activity.

Authors:  Yu Mu; Yi Jiang; Xiaodan Qu; Bo Liu; Junfeng Tan; Guiding Li; Mingguo Jiang; Liya Li; Li Han; Xueshi Huang
Journal:  RSC Adv       Date:  2021-10-28       Impact factor: 4.036

Review 6.  The Implications of the Brønsted Acidic Properties of Crabtree-Type Catalysts in the Asymmetric Hydrogenation of Olefins.

Authors:  Bram B C Peters; Pher G Andersson
Journal:  J Am Chem Soc       Date:  2022-08-31       Impact factor: 16.383

7.  Short, Tin-Free Synthesis of All Three Inthomycins.

Authors:  Manjeet Kumar; Liam Bromhead; Zoe Anderson; Alistair Overy; Jonathan W Burton
Journal:  Chemistry       Date:  2018-10-19       Impact factor: 5.236

8.  Kinetic resolution of racemic allylic alcohols via iridium-catalyzed asymmetric hydrogenation: scope, synthetic applications and insight into the origin of selectivity.

Authors:  Haibo Wu; Cristiana Margarita; Jira Jongcharoenkamol; Mark D Nolan; Thishana Singh; Pher G Andersson
Journal:  Chem Sci       Date:  2020-12-08       Impact factor: 9.825
  8 in total

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