Literature DB >> 16930042

Synthetic study of 1,3-butadiene-based IMDA approach to construct a [5-7-6] tricyclic core and its application to the total synthesis of C8-epi-guanacastepene O.

Chuang-Chuang Li1, Cui-Hua Wang, Bo Liang, Xin-Hao Zhang, Lu-Jiang Deng, Shuang Liang, Jia-Hua Chen, Yun-Dong Wu, Zhen Yang.   

Abstract

An efficient intramolecular Diels-Alder (IMDA) strategy for the construction of the [5-7-6] tricyclic core (18) of guanacastepenes has been developed from cis- and trans-1,3-butadiene-tethered 4-oxopent-2-ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.

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Year:  2006        PMID: 16930042     DOI: 10.1021/jo060996h

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


  4 in total

1.  Development of a catalytic enantioselective synthesis of the guanacastepene and heptemerone tricyclic core.

Authors:  Andrew M Harned; Brian M Stoltz
Journal:  Tetrahedron       Date:  2019-02-27       Impact factor: 2.457

2.  Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

Authors:  Junjia Liu; T Aaron Bedell; Julian G West; Erik J Sorensen
Journal:  Tetrahedron       Date:  2016-01-28       Impact factor: 2.457

3.  Five New Guanacastane-Type Diterpenes from Cultures of the Fungus Psathyrella candolleana.

Authors:  Xia Yin; Tao Feng; Zheng-Hui Li; Ying Leng; Ji-Kai Liu
Journal:  Nat Prod Bioprospect       Date:  2014-05-08

Review 4.  Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010-2020).

Authors:  Fa-Lei Zhang; Tao Feng
Journal:  J Fungi (Basel)       Date:  2022-02-28
  4 in total

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