Currently the development of methods in organic synthesis is largely carried out on an ad hoc basis by determining the best retrosynthesis for each natural product in isolation. Conversely, we carried out a systematic deconstructive analysis of all linear natural products which reveals a prioritized list of building blocks and the required couplings to collectively access greater than 75% of the chemical space they occupy. For each coupling, analysis of the local chemical environment to a breadth of two heavy atoms reveals the necessary substrate scope to achieve a general coupling methodology. Preliminary analysis into primary Csp3 boronates coupling to vinyl halides suggests that highly stereospecific couplings are accessible for E and Z olefins. Current efforts are aimed at extending the generality of this method to achieve the broad substrate scope required for generalized natural product synthesis.

En masse analysis yields prioritized blocks and bonds for natural product synthesis

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.