Toward a formal synthesis of laureatin: Unexpected rearrangements involving cyclic ether nucleophiles

Santosh Keshipeddy, Isamir Martíez, Bernard F. Castillo, Martha D. Morton, Amy R. Howell

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Laureatin, a metabolite of the red algae Laurencia nipponica, has shown potent activity as a mosquito larvicide. The two previously published syntheses of laureatin involved an initial preparation of the 8-membered cyclic ether, followed by formation of the oxetane ring. Our strategy was the reverse, i.e., to utilize an oxetane as the framework to construct the larger ring. During this work, attempted Nbromosuccinimide (NBS)-mediated cyclization of oxetane alcohol 17, prepared from readily accessible 2-methyleneoxetane 12, yielded epoxytetrahydrofuran 19 rather than the expected laureatin core. Further derivatization of 19 yielded trans fused bistetrahydrofuran 32. The synthesis of 19 and 32, as well as structural and stereochemical elucidation studies, are described.

Original languageEnglish (US)
Pages (from-to)7883-7890
Number of pages8
JournalJournal of Organic Chemistry
Volume77
Issue number18
DOIs
StatePublished - Sep 21 2012

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Cyclic Ethers
Nucleophiles
Cyclization
Algae
Metabolites
Alcohols
oxetane
laureatin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Toward a formal synthesis of laureatin : Unexpected rearrangements involving cyclic ether nucleophiles. / Keshipeddy, Santosh; Martíez, Isamir; Castillo, Bernard F.; Morton, Martha D.; Howell, Amy R.

In: Journal of Organic Chemistry, Vol. 77, No. 18, 21.09.2012, p. 7883-7890.

Research output: Contribution to journalArticle

Keshipeddy, Santosh ; Martíez, Isamir ; Castillo, Bernard F. ; Morton, Martha D. ; Howell, Amy R. / Toward a formal synthesis of laureatin : Unexpected rearrangements involving cyclic ether nucleophiles. In: Journal of Organic Chemistry. 2012 ; Vol. 77, No. 18. pp. 7883-7890.
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