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Synthesis of the C(29)-C(45) bis-pyran subunit (E-F) of spongistatin 1 (Altohyrtin A)

Academic Article
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Overview

authors

  • Micalizio, Glenn
  • Pinchuk, A. N.
  • Roush, William

publication date

  • December 2000

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A synthesis of the C(29)-C(45) bis-pyran subunit 2 of spongistatin 1 (1a) is described. The synthesis proceeds in 19 steps from the chiral aldehyde ent-7, and features highly diastereoselective alpha-alkoxyallylation reactions using the gamma-alkoxy substituted allylstannanes 17 and 19, as well as a thermodynamically controlled intramolecular Michael addition to close the F-ring pyran. The E ring was assembled via the Mukaiyama aldol reaction of F-ring methyl ketone 3 and the 2,3-syn aldehyde 4.

subject areas

  • Ethers, Cyclic
  • Lactones
  • Macrolides
  • Pyrans
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo001236o

PubMed ID

  • 11112596
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Additional Document Info

start page

  • 8730

end page

  • 8736

volume

  • 65

issue

  • 25

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