The total synthesis of (-)-aplysin via a lithiation-borylation-propenylation sequence

Catherine J. Fletcher, Daniel J. Blair, Katherine M. P. Wheelhouse, Varinder K. Aggarwal*

*Corresponding author for this work

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

19 Citations (Scopus)

Abstract

A concise, highly enantioselective synthesis of sesquiterpene natural products (-)-debromoaplysin and (-)-aplysin has been completed. The key steps included lithiation-borylation of a secondary benzylic carbamate to give a tertiary boronic ester followed by propenylation which installed the quaternary stereocenter with complete enantioselectivity. Subsequent RCM followed by deprotection and in situ cyclization led to debromoaplysin with good diastereoselectivity from which the target compound was prepared in just eight overall steps. (C) 2012 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)7598-7604
Number of pages7
JournalTetrahedron
Volume68
Issue number37
DOIs
Publication statusPublished - 16 Sep 2012

Keywords

  • Lithiation-borylation
  • Quaternary stereocenter
  • Aplysin
  • Total synthesis
  • Sesquiterpene
  • ASYMMETRIC TRANSFER HYDROGENATION
  • RING-CLOSING METATHESIS
  • FORMAL TOTAL-SYNTHESIS
  • LAURENCIA-FILIFORMIS
  • OLEFIN METATHESIS
  • (-)-DEBROMOAPLYSIN
  • ENANTIOSELECTIVITY
  • SESQUITERPENES
  • ALCOHOLS
  • APLYSIN

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