Literature DB >> 24223440

Total Syntheses of Proposed (±)-Trichodermatides B and C.

Qian Li1, Yan-Shuang Xu, Gregory A Ellis, Timothy S Bugni, Yu Tang, Richard P Hsung.   

Abstract

Total syntheses of putative (±)-trichodermatides B and C are described. These efficient syntheses feature the oxa-[3 + 3] annulation strategy, leading to B and C along with their respective C2-epimers. However, these synthetic samples are spectroscopically very different from the natural products. DFT calculations of C13 chemical shifts are conducted and the predicted values are in good agreement with those of synthetic samples, thereby questioning in the accuracy of structural assignments of trichodermatides B and C.

Entities:  

Keywords:  DFT calculations; Davis’ oxaziridine; Trichodermatides; biosynthesis; electrocyclic ring-opening; oxa-[3 + 3] annulation

Year:  2013        PMID： 24223440      PMCID： PMC3818125          DOI： 10.1016/j.tetlet.2013.07.137

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  30 in total

1.  Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability.

Authors:  Steven G Smith; Jonathan M Goodman
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

Review 2.  A case study in biomimetic total synthesis: polyolefin carbocyclizations to terpenes and steroids.

Authors:  Ryan A Yoder; Jeffrey N Johnston
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

3.  Investigation of an organomagnesium-based [3 + 3] annelation to pyrans and its application in the synthesis of rhopaloic acid A.

Authors:  Julien C R Brioche; Katharine M Goodenough; David J Whatrup; Joseph P A Harrity
Journal:  J Org Chem       Date:  2008-02-07       Impact factor: 4.354

4.  A concise synthesis of the pentacyclic framework of cortistatins.

Authors:  Shuji Yamashita; Kentaro Iso; Masahiro Hirama
Journal:  Org Lett       Date:  2008-07-17       Impact factor: 6.005

5.  Total synthesis of cortistatins A and J.

Authors:  Shuji Yamashita; Kentaro Iso; Kazuki Kitajima; Masafumi Himuro; Masahiro Hirama
Journal:  J Org Chem       Date:  2011-03-15       Impact factor: 4.354

6.  Total Synthesis of Tovophyllin B.

Authors:  Valer Jeso; K C Nicolaou
Journal:  Tetrahedron Lett       Date:  2009-03-18       Impact factor: 2.415

7.  PPh3-catalyzed (3 + 3) annulations of 5-acetoxypenta-2,3-dienoate with 1C,3O-bisnucleophiles: facile entry to stable monocyclic 2H-pyrans.

Authors:  Jian Hu; Wei Dong; Xin-Yan Wu; Xiaofeng Tong
Journal:  Org Lett       Date:  2012-10-23       Impact factor: 6.005

8.  Asymmetric total syntheses of (-)-penicipyrone and (-)-tenuipyrone via biomimetic cascade intermolecular Michael addition/cycloketalization.

Authors:  Liyan Song; Hongliang Yao; Liangyu Zhu; Rongbiao Tong
Journal:  Org Lett       Date:  2012-12-18       Impact factor: 6.005

9.  Total synthesis of phomactin A.

Authors:  Yu Tang; Kevin P Cole; Grant S Buchanan; Gang Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

10.  Koninginin C: a biologically active natural product from Trichoderma koningii.

Authors:  S R Parker; H G Cutler; P R Schreiner
Journal:  Biosci Biotechnol Biochem       Date:  1995-06       Impact factor: 2.043
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.