440660-21-9Relevant academic research and scientific papers
Studies on the synthesis of (-)-spinosyn A: Application of the steric directing group strategy to transannular Diels-Alder reactions
Frank, Scott A.,Roush, William R.
, p. 4316 - 4324 (2002)
A highly diastereoselective and enantioselective synthesis of the decahydro-as-indacene nucleus 12 of (-)-spinosyn A (1) is reported. By implementing the steric directing group strategy, tricyclic lactone 37 was produced from a remarkably diastereoselective transannular Diels-Alder reaction of lactone 9. The tricyclic core of the natural product was then obtained by using an Ireland-Claisen ring contraction of 37. Reversal of the order of these two steps resulted in an almost complete loss of diastereoselectivity.
