Literature DB >> 19485348

Concise total synthesis of (+)-aspergillide B.

Jian Liu1, Ke Xu, Jinmei He, Ling Zhang, Xinfu Pan, Xuegong She.   

Abstract

An efficient total synthesis of (+)-aspergillide B has been achieved, which features the C-glycosylation reaction for constructing the 2,6-trans-substituted pyran core, a highly effective four-step sequence without purification to produce the key intermediate 13 and an advantegous E-selective Julia-Kocienski olefination on a highly elaborate substrate. The synthesis confirmed the revised structure of aspergillide B by Uenishi.

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Year:  2009        PMID: 19485348     DOI: 10.1021/jo900820f

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


  5 in total

Review 1.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

2.  Total synthesis of iejimalide B.

Authors:  Qingshou Chen; Dirk Schweitzer; John Kane; V Jo Davisson; Paul Helquist
Journal:  J Org Chem       Date:  2011-04-20       Impact factor: 4.354

3.  Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

Authors:  Barry M Trost; Mark J Bartlett
Journal:  Org Lett       Date:  2012-02-22       Impact factor: 6.005

4.  Enantioselective formal total synthesis of (+)-aspergillide C.

Authors:  Joseph D Panarese; Stephen P Waters
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

5.  A carbohydrate approach for the formal total synthesis of (-)-aspergillide C.

Authors:  Pabbaraja Srihari; Namballa Hari Krishna; Ydhyam Sridhar; Ahmed Kamal
Journal:  Beilstein J Org Chem       Date:  2014-12-23       Impact factor: 2.883

  5 in total

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