GENERAL APPROACH FOR THE SYNTHESIS OF MACROLINE/SARPAGINE ALKALOIDS. THE TOTAL SYNTHESIS OF (+)-MACROLINE

Article abstract of DOI:10.1016/0040-4039(93)88069-U

(+)-Macroline 1 and a more stable equivalent 2 were synthesized from the tetracyclic ketone 5.The key steps in the synthesis involved a stereoselective Claisen rearrangement followed by hydroboration-oxidation of the resulting olefin 14 to set the correct stereochemistry at C-15 and C-16.