Synthesis of (-)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition-Rearrangement and Cross-electrophile Coupling

Younes Fegheh-Hassanpour, Tanzeel Arif, Herman O. Sintim, Hamad H. Al Mamari, David M. Hodgson

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

An asymmetric synthesis of (-)-6,7-dideoxysqualestatin H5 is reported. Key features of the synthesis include the following: (1) highly diastereoselective n-alkylation of a tartrate acetonide enolate and subsequent oxidation-hydrolysis to provide an asymmetric entry to a β-hydroxy-α-ketoester motif; (2) facilitation of Rh(II)-catalyzed cyclic carbonyl ylide formation-cycloaddition by co-generation of keto and diazo functionality through ozonolysis of an unsaturated hydrazone; and (3) stereoretentive Ni-catalyzed Csp3-Csp2 cross-electrophile coupling between tricarboxylate core and unsaturated side chain to complete the natural product.

Original languageEnglish
Pages (from-to)3540-3543
Number of pages4
JournalOrganic Letters
Volume19
Issue number13
DOIs
Publication statusPublished - Jul 7 2017

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Hydrazones
Cycloaddition
cross coupling
Cycloaddition Reaction
Alkylation
cycloaddition
Biological Products
Hydrolysis
cogeneration
hydrazones
alkylation
synthesis
entry
hydrolysis
Oxidation
oxidation
products
6,7-dideoxysqualestatin H5
tartaric acid

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of (-)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition-Rearrangement and Cross-electrophile Coupling. / Fegheh-Hassanpour, Younes; Arif, Tanzeel; Sintim, Herman O.; Al Mamari, Hamad H.; Hodgson, David M.

In: Organic Letters, Vol. 19, No. 13, 07.07.2017, p. 3540-3543.

Research output: Contribution to journalArticle

Fegheh-Hassanpour, Younes ; Arif, Tanzeel ; Sintim, Herman O. ; Al Mamari, Hamad H. ; Hodgson, David M. / Synthesis of (-)-6,7-Dideoxysqualestatin H5 by Carbonyl Ylide Cycloaddition-Rearrangement and Cross-electrophile Coupling. In: Organic Letters. 2017 ; Vol. 19, No. 13. pp. 3540-3543.
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