Literature DB >> 19860426

Total synthesis and absolute stereochemistry of integric acid.

Dennis C J Waalboer1, Henri A van Kalkeren, Mark C Schaapman, Floris L van Delft, Floris P J T Rutjes.   

Abstract

An efficient total synthesis of integric acid is described starting from the Wieland-Miescher ketone. Key steps involve a one-step orthogonal deprotection/protection strategy of a thioacetal/aldehyde and the selective oxidative cleavage of a prenyl group in the presence of two other unsaturated moieties. The synthesis of both C4' diastereoisomers of integric acid delivered unambiguous evidence for (S)-stereochemistry at the C4' position.

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Year:  2009        PMID: 19860426     DOI: 10.1021/jo901845r

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  1 in total

1.  Biosynthesis of integric acid isolated from the wood-decay fungus Xylaria feejeensis 2FB-PPM08M.

Authors:  Totsaporn Srisapoomi; Tsuyoshi Ichiyanagi; Hiromitsu Nakajima; Tadanori Aimi; Sophon Boonlue
Journal:  Curr Microbiol       Date:  2014-12-17       Impact factor: 2.188

  1 in total

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