Two Steps to Bicyclo[4.2.0]octadienes from Cyclooctatetraene: Total Synthesis of Kingianic Acid A

Harshal D. Patel, Thomas Fallon

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Synthetic approaches to bicyclo[4.2.0]octadiene natural products frequently employ the synthesis of linear tetraenes to initiate a biosynthetic 8π/6π-electrocyclization cascade. This work forges a functionalized bicyclo[4.2.0]octadiene in two steps from cyclooctatetraene. The versatility of this method is demonstrated through natural product synthesis, including the first total synthesis of kingianic acid A and formal syntheses of kingianins A, D, and F and cryptobeilic acid D ethyl ester. The unexpected formation of an E,E,Z,E-tetraene byproduct is rationalized through density functional theory modeling.

Original languageEnglish
Pages (from-to)2276-2281
Number of pages6
JournalOrganic Letters
Volume24
Issue number12
Early online date16 Mar 2022
DOIs
Publication statusPublished - 1 Apr 2022
Externally publishedYes

Keywords

  • Cyclooctatetraene
  • Endiandric acids
  • Tetraenes
  • Bicyclo[4.2.0]octadienes

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