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 language | English |
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Pages (from-to) | 2276-2281 |
Number of pages | 6 |
Journal | Organic Letters |
Volume | 24 |
Issue number | 12 |
Early online date | 16 Mar 2022 |
DOIs | |
Publication status | Published - 1 Apr 2022 |
Externally published | Yes |
Keywords
- Cyclooctatetraene
- Endiandric acids
- Tetraenes
- Bicyclo[4.2.0]octadienes