Synthesis of the Proposed Structure of Cryptoconcatone H
Expedient Synthesis of the Proposed Structure of Cryptoconcatone H Exploiting Hidden Symmetry: H. G. Ford, E. C. Hastry, J. B. Choi, C. J. Terranova, K. J. Quinn
Synlett 2022, DOI: 10.1055/a-1972-3587
Cryptoconcatones are natural products isolated from the leaves and branches of an evergreen plant found in subtropical mainland China. The initially proposed structure of cryptoconcatone H, one of the members of this family of compounds, was called into question soon after its initial publication and subsequently revised by reassigning the configuration of two of the four stereogenic centers. To continue towards the goal of assigning the correct structures to all the cryptoconcatones, the group of Professor Kevin J. Quinn from the College of the Holy Cross (Worcester, USA) recently reported the efficient synthesis of the originally proposed structure of cryptoconcatone H.
Professor Quinn said: “Our team of undergraduate researchers have completed a total synthesis of the originally proposed structure of the tetrahydropyranol-dihydropyranone natural product cryptoconcatone H in just three steps and 32% overall yield. The synthesis illustrates the step economy and efficiency imparted by the recognition of hidden symmetry in retrosynthetic planning and streamlining effect it can provide in organic synthesis.”