Efficient Synthesis of Cylindol A and the Proposed Structure of Cylindol B: The Structure of Cylindol B Still in Question

Highly efficient syntheses of cylindol A (1) and the proposed structure of cylindol B (2) have been accomplished using common synthetic transformations from symmetrical starting materials 7 and 11, respectively. The latter synthesis revealed that the proposed structure of the natural cylindol B was assigned incorrectly. Isomers of 2 such as 15 and 16 were synthesized as a possible candidate of the natural cylindol B. However, their spectral data also did not match that of the natural cylindol B. Therefore, the structure of the natural cylindol B is yet to be resolved.