Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis

Adam Noble, Stefan Roesner, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

24 Citations (Scopus)
306 Downloads (Pure)

Abstract

Short and highly stereoselective total syntheses of the sesquilignan natural product tatanan A and its C3 epimer are described. An assembly-line synthesis approach, using iterative lithiation–borylation reactions, was applied to install the three contiguous stereocenters with high enantio- and diastereoselectivity. One of the stereocenters was installed using a configurationally labile lithiated primary benzyl benzoate, resulting in high levels of substrate-controlled (undesired) diastereoselectivity. However, reversal of selectivity was achieved by using a novel diastereoselective Matteson homologation. Stereospecific alkynylation of a hindered secondary benzylic boronic ester enabled completion of the synthesis in a total of eight steps.

Original languageEnglish
Pages (from-to)15920-15924
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number51
Early online date16 Nov 2016
DOIs
Publication statusPublished - 19 Dec 2016

Keywords

  • alkynylation
  • lithiation–borylation
  • Matteson homologation
  • tatanan A
  • total synthesis

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