Formal Synthesis of (+)-Phomactin A via a Prins/Conia-ene Cascade and γ-Hydroxylation Strategy

Lantian Sun, Junrong Huang*, Bo Wang, Guangyan Du, Chi-Sing Lee*

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

1 Citation (Scopus)

Abstract

An asymmetric formal synthesis of (+)-phomactin A has been accomplished. The key steps in the synthetic strategy included establishing the AB ring system in one-pot via Prins/Conia-ene cascade cyclization reaction and the C ring formation via γ-hydroxylation of enone in the late-stage of the synthesis. The two major fragments are readily prepared from (+)-pulegone and geraniol via a modified Eschenmoser–Tanabe fragmentation strategy in 6 steps and a Sharpless asymmetric epoxidation/hydrozirconation/ Roskamp reaction sequence in 11 steps respectively.
Original languageEnglish
Article numbere202304204
Number of pages11
JournalChemistrySelect
Volume8
Issue number42
Early online date9 Nov 2023
DOIs
Publication statusPublished - 13 Nov 2023

Scopus Subject Areas

  • Chemistry(all)

User-Defined Keywords

  • Conia-ene reaction
  • Prins reaction
  • formal synthesis
  • phomactin A
  • γ-hydroxylation

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