Literature DB >> 11325217

A formal total synthesis of racemic sesquiterpenoid sativene.

S Karimi1.   

Abstract

Several key reactions involving intramolecular cyclization, Grignard reaction, and ionic hydrogenation have been employed in a formal synthesis of sativene. The synthesis affords 3-isopropyl-6-methyltricyclo[4.4.0.0(2,8)]decan-7-one, 12, McMurry's penultimate precursor to sativene, in 28% overall yield in eight steps starting with the commercially available racemic Wieland--Miescher ketone.

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Year:  2001        PMID: 11325217     DOI: 10.1021/np000550a

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  4 in total

1.  Evolution of an oxidative dearomatization enabled total synthesis of vinigrol.

Authors:  Qingliang Yang; Cristian Draghici; Jon T Njardarson; Fang Li; Brandon R Smith; Pradipta Das
Journal:  Org Biomol Chem       Date:  2014-01-14       Impact factor: 3.876

2.  Seco-sativene and Seco-longifolene Sesquiterpenoids from Cultures of Endophytic Fungus Bipolaris eleusines.

Authors:  Man-Si Yang; Xiao-Yue Cai; Yuan-Yuan He; Meng-Ying Lu; Shuang Liu; Wen-Xiang Wang; Zheng-Hui Li; Hong-Lian Ai; Tao Feng
Journal:  Nat Prod Bioprospect       Date:  2017-01-06

3.  Anti-phytopathogenic sesquiterpenoid-xanthone adducts from potato endophytic fungus Bipolaris eleusines.

Authors:  Juan He; Man-Si Yang; Wen-Xiang Wang; Zheng-Hui Li; Waill Ahmed Mohamed Elkhateeb; Ting-Chi Wen; Hong-Lian Ai; Tao Feng
Journal:  RSC Adv       Date:  2018-12-21       Impact factor: 4.036

4.  Volatile compound-mediated interactions between barley and pathogenic fungi in the soil.

Authors:  Marie Fiers; Georges Lognay; Marie-Laure Fauconnier; M Haïssam Jijakli
Journal:  PLoS One       Date:  2013-06-20       Impact factor: 3.240

  4 in total

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