Literature DB >> 19166346

Synthesis of (+)- and (-)-monanchorin.

Min Yu1, Barry B Snider.   

Abstract

The optically pure epoxy acetal was converted to the protected guanidino alcohol by reaction with NaN(3) in DMF, hydrogenation of the azide, and reaction of the amine with MeSC(NBoc)NHBoc, AgNO(3), and Et(3)N. Treatment of the protected guanidino alcohol with 9:1 CDCl(3)/TFA afforded monanchorin, whose absolute stereochemistry was assigned as shown.

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Year:  2009        PMID: 19166346      PMCID: PMC2661423          DOI: 10.1021/ol802981h

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


  5 in total

1.  Synthesis of C2-symmetric guanidino-sugars as potent inhibitors of glycosidases.

Authors:  Y Le Merrer; L Gauzy; C Gravier-Pelletier; J C Depezay
Journal:  Bioorg Med Chem       Date:  2000-02       Impact factor: 3.641

2.  First total synthesis of martinellic acid, a naturally occurring bradykinin receptor antagonist.

Authors:  D Ma; C Xia; J Jiang; J Zhang
Journal:  Org Lett       Date:  2001-07-12       Impact factor: 6.005

3.  Practical synthesis of an L-fructose-derived ketone catalyst for asymmetric epoxidation of olefins.

Authors:  Mei-Xin Zhao; Yian Shi
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

4.  Monanchorin, a bicyclic alkaloid from the sponge Monanchora ungiculata.

Authors:  Karina M Meragelman; Tawnya C McKee; James B McMahon
Journal:  J Nat Prod       Date:  2004-07       Impact factor: 4.050

5.  Synthesis of 7-epineoptilocaulin, mirabilin B, and isoptilocaulin. A unified biosynthetic proposal for the ptilocaulin and batzelladine alkaloids. Synthesis and structure revision of netamines E and G.

Authors:  Min Yu; Susan S Pochapsky; Barry B Snider
Journal:  J Org Chem       Date:  2008-10-18       Impact factor: 4.354

  5 in total
  1 in total

1.  Synthesis of phidianidines A and B.

Authors:  Hong-Yu Lin; Barry B Snider
Journal:  J Org Chem       Date:  2012-05-01       Impact factor: 4.354

  1 in total

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