Literature DB >> 19382764

Asymmetric total synthesis and revision of the absolute configuration of 4-keto-clonostachydiol.

Junjie Han1, Yingpeng Su, Tuo Jiang, Yanfen Xu, Xing Huo, Xuegong She, Xinfu Pan.   

Abstract

The first total synthesis of the 14-membered natural macrocyclic bislactone 4-keto-clonostachydiol, along with its enantiomer, has been accomplished in 13 steps with overall yields of 8.4% and 8.0%, respectively. The absolute configuration of 4-keto-clonostachydiol 1 has been revised as (5S,10S,13S).

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Year:  2009        PMID: 19382764     DOI: 10.1021/jo900370a

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

Review 1.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

2.  Opportunities and Limitations for Assigning Relative Configurations of Antibacterial Bislactones using GIAO NMR Shift Calculations.

Authors:  Sonja L Knowles; Christopher D Roberts; Mario Augustinović; Laura Flores-Bocanegra; Huzefa A Raja; Kimberly N Heath-Borrero; Joanna E Burdette; Joseph O Falkinham Iii; Cedric J Pearce; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2021-03-25       Impact factor: 4.050

3.  Isolation and Structure Elucidation of New Cytotoxic Macrolides Halosmysins B and C from the Fungus Halosphaeriaceae sp. Associated with a Marine Alga.

Authors:  Takeshi Yamada; Kanoko Yoshida; Takashi Kikuchi; Tomoya Hirano
Journal:  Mar Drugs       Date:  2022-03-25       Impact factor: 6.085

4.  Halosmysin A, a Novel 14-Membered Macrodiolide Isolated from the Marine-Algae-Derived Fungus Halosphaeriaceae sp.

Authors:  Takeshi Yamada; Haruka Kogure; Minami Kataoka; Takashi Kikuchi; Tomoya Hirano
Journal:  Mar Drugs       Date:  2020-06-18       Impact factor: 5.118

Review 5.  Marine-Derived Macrolides 1990-2020: An Overview of Chemical and Biological Diversity.

Authors:  Hairong Zhang; Jiabin Zou; Xiaoxue Yan; Junlong Chen; Xiujiao Cao; Jialing Wu; Yinghui Liu; Tingting Wang
Journal:  Mar Drugs       Date:  2021-03-25       Impact factor: 5.118

  5 in total

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