Stereocontrolled construction of the trans-tetrahydrofuran units in Annonaceous acetogenins

  • 10.1016/s0957-4166(99)00259-1
  • Tetrahedron: Asymmetry
  • p 2551-2562, Volume 10, Issue 13,
  • journal-article
Abstract An efficient synthetic method for the construction of trans-tetrahydrofuran (THF) unit from trans-1,5,9-decatriene was successfully developed by means of Sharpless AD reactions and oxidative cyclizations catalyzed by Co(modp)2 under an oxygen atmosphere. Based on this new synthetic strategy, the trans-mono-THF unit, trans-bis-THF unit and trans-tris-THF unit in Annonaceous acetogenins were smoothly obtained.


Experimental not reproducible as written

Procedure for synthesis of intermediate 2 was repeated three times at identical scale and reaction conditions as described and then modified. When followed exact same procedure as-written (12 hours), desired compound was obtained in 14% yield (confirmed by NMR) and major...