Literature DB >> 27910244

Total Syntheses of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers.

Changchun Yuan1, Biao Du1, Heping Deng1, Yi Man1, Bo Liu1,2.   

Abstract

The syntheses of members of a family of lindenane sesquiterpenoid [4+2] dimers led to the total syntheses of sarcandrolide J and shizukaol D. Inspired by a modified biosynthetic pathway, a cascade featuring furan formation/alkene isomerization/Diels-Alder cycloaddition was devised to construct the congested polycyclic architecture of the target molecules with the correct stereochemistry. This study presents a pioneering synthetic entry to this family of natural products and paves the way for fully exploring their biological functions.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biomimetic synthesis; cycloaddition; natural products; terpenoids; total synthesis

Mesh:

Substances:

Year:  2016        PMID: 27910244     DOI: 10.1002/anie.201610484

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

1.  Reanalysis of Lindenatriene, a Building Block for the Synthesis of Lindenane Oligomers.

Authors:  Ruben M Martinez; Hannah E Burdge; Ryan A Shenvi
Journal:  Tetrahedron       Date:  2019-03-14       Impact factor: 2.457

2.  Atypical Lindenane-Type Sesquiterpenes from Lindera myrrha.

Authors:  Thuc-Huy Duong; Mehdi A Beniddir; Nguyen T Trung; Cam-Tu D Phan; Van Giau Vo; Van-Kieu Nguyen; Quynh-Loan Le; Hoang-Dung Nguyen; Pierre Le Pogam
Journal:  Molecules       Date:  2020-04-16       Impact factor: 4.411

3.  A unified strategy toward total syntheses of lindenane sesquiterpenoid [4 + 2] dimers.

Authors:  Biao Du; Zhengsong Huang; Xiao Wang; Ting Chen; Guo Shen; Shaomin Fu; Bo Liu
Journal:  Nat Commun       Date:  2019-04-23       Impact factor: 14.919

4.  Total syntheses of shizukaols A and E.

Authors:  Jian-Li Wu; Yin-Suo Lu; Bencan Tang; Xiao-Shui Peng
Journal:  Nat Commun       Date:  2018-10-02       Impact factor: 14.919

  4 in total

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