Synthesis of E-deoxypukalide, and its biomimetic conversion into deoxypseudopterolide by photochemical ring contraction involving a 1,3-allylic shift

Zhi Yang, Yi Li, Gerald Pattenden*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


Irradiation of a solution of synthetic Z-deoxypukalide 10 in acetonitrile (Pyrex; 400 W Hg lamp) resulted in isomerisation, leading to E-deoxypukalide 12, which was isolated recently from the octocoral Leptogorgia spp. Further irradiation of 12, or prolonged irradiation of 10, then gave the ring-contracted product, deoxypseudopterolide 1 (>90%) found in octocorals of the genera Pseudopterogorgia and Leptogorgia. The contraction of the 14-membered rings in 10 and 12 to the 12-membered ring as 1, occurs by way of photochemical [1,3]-sigmatropic rearrangement.

Original languageEnglish
Pages (from-to)6546-6549
Number of pages4
Issue number33
Publication statusPublished - 14 Aug 2010
Externally publishedYes


  • 1,3-Allylic shift, [1,3] Sigmatropic rearrangement
  • Deoxypseudopterolide
  • E-Deoxypukalide
  • Octocorals
  • Photochemical ring contraction

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