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Enantioselective synthesis of (-)-basiliskamide A

Academic Article
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Overview

related to degree

  • Chen, Ming, Ph.D. in Organic Chemistry, Scripps Research 2007 - 2012

authors

  • Chen, Ming
  • Roush, William

publication date

  • March 2012

journal

  • Organic Letters  Journal

abstract

  • Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available ?-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric ?-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.
  • Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available β-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric δ-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.

subject areas

  • Aldehydes
  • Antifungal Agents
  • Bacillus
  • Biological Products
  • Polyketides
  • Stereoisomerism
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Identity

PubMed Central ID

  • PMC3306514

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol300282e

PubMed ID

  • 22372693
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Additional Document Info

start page

  • 1556

end page

  • 1559

volume

  • 14

issue

  • 6

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