Our paper entitled “Diversity-oriented synthesis of Lycopodium alkaloids inspired by the hidden functional group pairing pattern” has been published on Nature Communications. In this study, we report a new concept of Functional Group Pairing Pattern Recognition (FGPPR) to facilitate both target-oriented synthesis of complex natural product and diversity-oriented synthesis of natural product-like scaffolds in parallel. […]
Our paper entitled “Diversity-oriented synthesis of Lycopodium alkaloids inspired by the hidden functional group pairing pattern” has been published on Nature Communications. In this study, we report a new concept of Functional Group Pairing Pattern Recognition (FGPPR) to facilitate both target-oriented synthesis of complex natural product and diversity-oriented synthesis of natural product-like scaffolds in parallel.
Abstract:
Natural products continue to provide a rich source of inspiration for both chemists and biologists. The efficient synthesis of bioactive natural products or natural product-like molecules has offered tremendous opportunities for complex biological processes exploration and drug discovery. However, because natural products usually contain numerous stereogenic centres and polycyclic ring systems, significant synthetic challenges remain. Here we employ the build/couple/pair strategy that is frequently used in diversity-oriented synthesis to obtain skeletally diverse compounds with complexities comparable to natural products. Inspired by the functional group pairing patterns hidden in Lycopodium alkaloids, we efficiently and in parallel construct four natural products, (+)-Serratezomine A, (-)-Serratinine, (+)-8a-Hydroxyfawcettimine and (-)-Lycoposerramine-U, as well as six different unnatural scaffolds, following the advanced build/couple/pair algorithm. This newly developed strategy is expected to be applied to the efficient synthesis of other complex natural products possessing functional group pairing patterns as well as skeletally diverse natural product-like molecules.
Zhang, J. et al. Diversity-oriented synthesis of Lycopodium alkaloids inspired by the hidden functional group pairing pattern. Nat. Commun. 5:4614 doi: 10.1038/ncomms5614 (2014).