Nature has produced most natural molecules as chiral objects, which means the molecule can come in two enantiomeric forms, each being the mirror image of the other. When a natural product is synthesised in a laboratory, a chiral synthesis means just one form is made, and then is compared with the natural product to see if it matches. Just such a process was following in the recent synthesis of cylindricine, a marine alkaloid[1] featured on the ACS molecule-of-the-week site. The authors noted that the absolute configuration of cylindricine as isolated naturally had remained unassigned, and as it happens one way of measuring the properties of the individual enantiomer – its optical rotation – had not been determined. So in part, the purpose of this synthesis was to determine the absolute configuration of this molecule. Here I explore this process.
References
- M. Piccichè, A. Pinto, R. Griera, J. Bosch, and M. Amat, "Total Synthesis of (−)-Cylindricine H", Organic Letters, vol. 24, pp. 5356-5360, 2022. http://dx.doi.org/10.1021/acs.orglett.2c02004