Literature DB >> 33925490

Total Synthesis and Structural Reassignment of Laingolide A.

Fusong Wu1, Tao Zhang1, Jie Yu1,2, Yian Guo1,2, Tao Ye1.   

Abstract

The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide.

Entities:  

Keywords:  laingolide A; structural reassignment; total synthesis

Year:  2021        PMID： 33925490     DOI： 10.3390/md19050247

Source DB:  PubMed          Journal:  Mar Drugs        ISSN： 1660-3397            Impact factor:   5.118


  28 in total

1.  Total synthesis and stereochemical reassignment of bisebromoamide.

Authors:  Xuguang Gao; Yuqing Liu; Shuqin Kwong; Zhengshuang Xu; Tao Ye
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

2.  The total synthesis and stereochemical assignment of scytonemin A.

Authors:  Junyang Liu; Lei Wang; Juefei Zhang; Zhengshuang Xu; Tao Ye
Journal:  Chem Commun (Camb)       Date:  2016-01-18       Impact factor: 6.222

Review 3.  Chasing molecules that were never there: misassigned natural products and the role of chemical synthesis in modern structure elucidation.

Authors:  K C Nicolaou; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-04       Impact factor: 15.336

4.  Total Synthesis and Stereochemical Assignment of Actinoranone.

Authors:  Yi-An Guo; Meng Zhao; Zhengshuang Xu; Tao Ye
Journal:  Chemistry       Date:  2017-02-20       Impact factor: 5.236

5.  Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.

Authors:  M Scholl; S Ding; C W Lee; R H Grubbs
Journal:  Org Lett       Date:  1999-09-23       Impact factor: 6.005

6.  Total synthesis of largamide B.

Authors:  Shiwei Qu; Ying Chen; Xiaoji Wang; Shipeng Chen; Zhengshuang Xu; Tao Ye
Journal:  Chem Commun (Camb)       Date:  2015-02-14       Impact factor: 6.222

7.  Cytotoxic halogenated macrolides and modified peptides from the apratoxin-producing marine cyanobacterium Lyngbya bouillonii from Guam.

Authors:  Susan Matthew; Lilibeth A Salvador; Peter J Schupp; Valerie J Paul; Hendrik Luesch
Journal:  J Nat Prod       Date:  2010-09-24       Impact factor: 4.050

8.  A general model for selectivity in olefin cross metathesis.

Authors:  Arnab K Chatterjee; Tae-Lim Choi; Daniel P Sanders; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2003-09-17       Impact factor: 15.419

9.  Chemo- and Regioselective Functionalization of Polyols through Catalytic C(sp(3))-C(sp(3)) Kumada-Type Coupling of Cyclic Sulfate Esters.

Authors:  Rodrigo Ramírez-Contreras; Bill Morandi
Journal:  Org Lett       Date:  2016-07-21       Impact factor: 6.005

10.  Total Synthesis and Stereochemical Assignment of Callyspongiolide.

Authors:  Jingjing Zhou; Bowen Gao; Zhengshuang Xu; Tao Ye
Journal:  J Am Chem Soc       Date:  2016-05-26       Impact factor: 15.419
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