Literature DB >> 24957611

The absolute configuration for inthomycin C: revision of previously published work with a reinstatement of the (3R)-configuration for (-)-inthomycin C.

Karl J Hale1, Susumi Hatakeyama, Fumiya Urabe, Jun Ishihara, Soraya Manaviazar, Milosz Grabski, Maciej Maczka.   

Abstract

Stereochemical evidence is presented to demonstrate that (-)-inthomycin C has (3R)- and not (3S)-stereochemistry. Careful reappraisal of the previously published work2-5 now indicates that the Hatakeyama, Hale, Ryu, and Taylor teams all have synthesized (-)-(3R)-inthomycin C. The newly measured [α]D of pure (-)-(3R)-inthomycin C (98% ee) is -7.9 (c 0.33, CHCl3) and not -41.5 (c 0.1, CHCl3) as was previously reported in 2012.

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Year:  2014        PMID: 24957611     DOI: 10.1021/ol501484t

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 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.  Progress in the total synthesis of inthomycins.

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

3.  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

  3 in total

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