A new synthesis of the phytotoxic 10-membered lactone herbarumin I

Article abstract of DOI:10.1016/j.tetasy.2009.03.034

Herbarumin I a phytotoxic 10-membered lactone has been synthesized from d-(-)-isoascorbic acid in 12 steps with an overall yield of 16.8%. The methodology involved in generating the stereogenic center at C-8 is a Sharpless asymmetric epoxidation, as well 1,2-asymmetric induction followed by macrolactonization via RCM.