Asymmetric Synthesis of AB Rings in ent-Kaurene Carbon Framework

Wenjing Ma*, Lizhi Zhu, Mengxun Zhang, Chising Lee

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The total synthesis of ent-kaurene natural products of Xerophilusin I, Neolaxiflorin L, Eriocalyxin B, 15-epi- Enmelol completed by diversity-oriented synthesis strategy. In this paper, the regioselectivity of Horner-Wadsworth-Emmons reaction was optimized, and a single Z configuration was transformed from Z/E mixture under acidic condition. Based on the conversion of a single configuration under mild acidic conditions, a mechanism for hydrogen bond-assisted Michael addition/retro-Michael elimination is proposed. The asymmetric Diels-Alder reaction with silylenol ether dienyl 3 and β-ketoate 1 as dienophile was developed. Using Cu(OTf)2 as Lewis acid and oxazoline as chiral ligand, AB-ring-skeleton was constructed with 65% yield and >19:1 dr value.

Original languageEnglish
Pages (from-to)580-589
Number of pages10
JournalChinese Journal of Organic Chemistry
Volume42
Issue number2
DOIs
Publication statusPublished - Feb 2022

Scopus Subject Areas

  • Organic Chemistry

User-Defined Keywords

  • Asymmetric Diels-Alder reaction
  • Ent-kaurane
  • Horner-Wadsworth-Emmons reaction
  • Regioselectivity
  • Homer-Wadsworth-Emmons reaction
  • regioselectivity
  • ent-kaurane
  • asymmetric Diels-Alder reaction

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