Literature DB >> 24953777

Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol.

Gangarajula Sudhakar1, Shruthi Bayya, Vilas D Kadam, Jagadeesh Babu Nanubolu.   

Abstract

The first stereoselective total synthesis of gonytolide C, which is a monomeric unit of an innate immune promoter gonytolide A, has been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing α-keto ester followed by the excellent diastereoselective intramolecular cyclization. The first total synthesis of gonytolide G has been achieved by the oxidation of benzylic methyl in gonytolide C. Additionally, total synthesis of lachnone C and a formal synthesis of blennolide C and diversonol have been achieved by this synthetic method.

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Year:  2014        PMID: 24953777     DOI: 10.1039/c4ob00950a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

1.  Asymmetric Synthesis of Gonytolide A: Strategic Use of an Aryl Halide Blocking Group for Oxidative Coupling.

Authors:  Xiaowei Wu; Takayuki Iwata; Adam Scharf; Tian Qin; Kyle D Reichl; John A Porco
Journal:  J Am Chem Soc       Date:  2018-04-25       Impact factor: 15.419

2.  Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "Shapeshifting" Properties.

Authors:  Tian Qin; Takayuki Iwata; Tanya T Ransom; John A Beutler; John A Porco
Journal:  J Am Chem Soc       Date:  2015-11-25       Impact factor: 15.419

3.  Asymmetric synthesis of chromanone lactones via vinylogous conjugate addition of butenolide to 2-ester chromones.

Authors:  Yi Li; Shuang Xin; Rui Weng; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2022-07-05       Impact factor: 9.969

  3 in total

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