Literature DB >> 11890806

Asymmetric total synthesis of (-)-VM55599: establishment of the absolute stereochemistry and biogenetic implications.

Juan F Sanz-Cervera1, Robert M Williams.   

Abstract

The first asymmetric biomimetic total synthesis of VM55599 (13) has been achieved utilizing an intramolecular Diels-Alder cycloaddition as a key step. The synthetic material was utilized to elucidate the absolute stereochemistry of the natural product. The results are discussed in terms of a unified biogenesis of the paraherquamides and VM55599.

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Year:  2002        PMID： 11890806     DOI： 10.1021/ja017425l

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  14 in total

1.  Intermolecular Diels-Alder Cycloaddition for the Construction of Bicyclo[2.2.2]diazaoctane Structures: Formal Synthesis of Brevianamide B and Premalbrancheamide.

Authors:  Jacob G Robins; Kyu J Kim; Alex J Chinn; John S Woo; Jonathan R Scheerer
Journal:  J Org Chem       Date:  2016-02-26       Impact factor: 4.354

2.  Studies on the Biosynthesis of the Stephacidin and Notoamide Natural Products: A Stereochemical and Genetic Conundrum.

Authors:  James D Sunderhaus; David H Sherman; Robert M Williams
Journal:  Isr J Chem       Date:  2011-04       Impact factor: 3.333

Review 3.  Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.

Authors:  Kenneth A Miller; Robert M Williams
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

Review 4.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

5.  Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids.

Authors:  Nicholas H Angello; Robert E Wiley; Tristan G Elmore; Ryan S Perry; Jonathan R Scheerer
Journal:  Org Lett       Date:  2018-08-10       Impact factor: 6.005

6.  Biosynthetic studies of the notoamides: isotopic synthesis of stephacidin A and incorporation into notoamide B and sclerotiamide.

Authors:  Jennifer M Finefield; Hikaru Kato; Thomas J Greshock; David H Sherman; Sachiko Tsukamoto; Robert M Williams
Journal:  Org Lett       Date:  2011-06-30       Impact factor: 6.005

7.  ORGANIC SYNTHESIS. Response to Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence".

Authors:  Zhiqiang Ma; Xiaolei Wang; Xiao Wang; Rodrigo A Rodriguez; Curtis E Moore; Shuanhu Gao; Xianghui Tan; Yuyong Ma; Arnold L Rheingold; Phil S Baran; Chuo Chen
Journal:  Science       Date:  2015-07-09       Impact factor: 47.728

8.  Calmodulin inhibitory activity of the malbrancheamides and various analogs.

Authors:  Kenneth A Miller; Mario Figueroa; Meriah W N Valente; Thomas J Greshock; Rachel Mata; Robert M Williams
Journal:  Bioorg Med Chem Lett       Date:  2008-10-17       Impact factor: 2.823

9.  Biomimetic total synthesis of malbrancheamide and malbrancheamide B.

Authors:  Kenneth A Miller; Timothy R Welch; Thomas J Greshock; Yousong Ding; David H Sherman; Robert M Williams
Journal:  J Org Chem       Date:  2008-03-18       Impact factor: 4.354

10.  Premalbrancheamide: synthesis, isotopic labeling, biosynthetic incorporation, and detection in cultures of Malbranchea aurantiaca.

Authors:  Yousong Ding; Thomas J Greshock; Kenneth A Miller; David H Sherman; Robert M Williams
Journal:  Org Lett       Date:  2008-10-10       Impact factor: 6.005
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