Literature DB >> 17824705

Enantioselective total synthesis of (-)-clavosolide B.

Jung Beom Son1, Min-ho Hwang, Wonsun Lee, Duck-Hyung Lee.   

Abstract

Enantioselective synthesis of 2, a revised structure for (-)-clavosolide B, was accomplished by a convergent approach, where syn-selective aldol, hydroxy-directed cyclopropanation, Mitsunobu inversion, Schmidt-type glycosylation, and macrolactonization reactions were utilized as key reactions. Comparison of 1H and 13C NMR spectra and optical rotation measurement confirmed the relative and absolute stereochemistry of clavosolide B (2).

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Year:  2007        PMID: 17824705     DOI: 10.1021/ol7015115

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Synthesis, thermal properties, and cytotoxicity evaluation of hydrocarbon and fluorocarbon alkyl β-D-xylopyranoside surfactants.

Authors:  Wenjin Xu; Gifty Osei-Prempeh; Carolina Lema; E Davis Oldham; Renato J Aguilera; Sean Parkin; Stephen E Rankin; Barbara L Knutson; Hans-Joachim Lehmler
Journal:  Carbohydr Res       Date:  2011-12-09       Impact factor: 2.104

2.  Cyanolide A, a glycosidic macrolide with potent Molluscicidal activity from the Papua New Guinea cyanobacterium Lyngbya bouillonii.

Authors:  Alban R Pereira; Christine F McCue; William H Gerwick
Journal:  J Nat Prod       Date:  2010-02-26       Impact factor: 4.050

3.  Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.

Authors:  Alba Millán; James R Smith; Jack L-Y Chen; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-14       Impact factor: 15.336

  3 in total

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