Biogenetic space-guided synthesis of rearranged terpenoids

Abstract

Biogenetic space-guided synthesis is a tool to design efficient chemical syntheses of complex terpenoids by evaluating their surrounding biogenetic space.

Bioinspired Skeletal Reorganization Approach for the Synthesis of Steroid Natural Products

“…The structural diversity and bioactivities of rearranged steroids render them attractive targets for synthetic chemists, and many syntheses have been accomplished, by our group and others, as covered in several elegant reviews. , During the course of our work on designing a synthetic blueprint for these molecules, we were intrigued by the question of how they are biosynthesized . It has been shown that considering proposed biosynthesis routes while rationally designing synthetic approaches can be an effective strategy for quickly and easily accessing structurally complex natural products from abundant, inexpensive and commercially available starting materials .…”

Strategic convergent synthesis en route to Veratrum steroidal alkaloids

“…These feedstocks are then transformed to the target NPs by harnessing skeletal rearrangement and/or selective C–C bond cleavage to edit the skeleton. 52–54 Additionally, various sp 3 C–H bond functionalization/oxidations 55 are employed to install the desired reactive functionalities onto the skeleton (Scheme 1Ca). 27 Given the limited availability of synthetic methods that allow for the desired chemical transformations in conjunction with the desired chemoselectivity, preparing highly functionalized complex NPs through semi-synthesis presents strategic and methodological challenges.…”