Formal total synthesis of enigmazole A

Andreas Meissner, Takayuki Kishi, Yuka Fujisawa, Yuto Murai, Hiroyoshi Takamura, Isao Kadota

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A stereoselective formal total synthesis of enigmazole A, a marine macrolide isolated from Cinachyrella enigmatica, is described. Lewis acid mediated intramolecular allylation of an α-acetoxy ether, prepared from alcohol and carboxylic acid fragments was carried out to construct the methylene THP ring with high stereoselectivity. The late-stage macrolactonization of the corresponding seco-acid provided a known synthetic intermediate of enigmazole A.

Original languageEnglish
Pages (from-to)4492-4495
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number51
DOIs
Publication statusPublished - Dec 19 2018

Fingerprint

Allylation
Stereoselectivity
Lewis Acids
Macrolides
Carboxylic Acids
Ether
Alcohols
Acids
enigmazole A

Keywords

  • Allylation
  • Convergent synthesis
  • Enigmazole A
  • Macrolide
  • Reductive acetylation
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Formal total synthesis of enigmazole A. / Meissner, Andreas; Kishi, Takayuki; Fujisawa, Yuka; Murai, Yuto; Takamura, Hiroyoshi; Kadota, Isao.

In: Tetrahedron Letters, Vol. 59, No. 51, 19.12.2018, p. 4492-4495.

Research output: Contribution to journalArticle

Meissner, A, Kishi, T, Fujisawa, Y, Murai, Y, Takamura, H & Kadota, I 2018, 'Formal total synthesis of enigmazole A', Tetrahedron Letters, vol. 59, no. 51, pp. 4492-4495. https://doi.org/10.1016/j.tetlet.2018.11.017
Meissner, Andreas ; Kishi, Takayuki ; Fujisawa, Yuka ; Murai, Yuto ; Takamura, Hiroyoshi ; Kadota, Isao. / Formal total synthesis of enigmazole A. In: Tetrahedron Letters. 2018 ; Vol. 59, No. 51. pp. 4492-4495.
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