Advances in the Semi-Synthesis of Triterpenoids

Abstract

Recent achievements in triterpenoid semi-synthesis have been accounted, which were divided into three parts according to the applied strategies, including functionalization strategy, C-skeleton modification strategy, and glycosylation strategy. In the functionalization strategy part, both functional group inter-conversions and new functional group installations on triterpenoid starting materials were included. As for the C-skeleton modification strategy section, the contents were further divided into three parts according to the applied tactics, including C-skeleton rearrangement, ring scission, and extra heterocyclic ring introduction tactics. Meanwhile, in the glycosylation strategy section, conspicuous achievements in semi-synthesis of both natural and artificial triterpene saponins were encompassed. In the whole account, the pivotal transformations that brought about striking chemical structure variations on the triterpenoid starting materials were highlighted, which would provide inspiration to investigators who have been engaged in or are going to enter this area.

Natural Product Synthesis: The Endless Quest for Unreachable Perfection

“…Semisynthesis is the specific case in which a molecule is synthesized using a natural product as the starting material . The flagship example of this approach is docetaxel and paclitaxel semisynthesis from 10-deacetylbaccatin III .…”

Strategic convergent synthesis en route to Veratrum steroidal alkaloids

“…5,[14][15][16][17][18][19][20][21][22][23][24][25] Over the last decade, semisynthesis has emerged as a powerful tool, enabling the synthesis of many complex NPs, particularly steroids and terpenoids. 26,27 Alternatively, convergent synthesis involves the preparation of multiple functionalized fragments, which are eventually assembled into the precursor and/or the final NPs. [28][29][30][31] Veratrum steroidal alkaloids are highly intricate alkaloids, all characterized by a typical C-nor-D-homo steroid skeleton.…”

“…5,14–25 Over the last decade, semi-synthesis has emerged as a powerful tool, enabling the synthesis of many complex NPs, particularly steroids and terpenoids. 26,27 Alternatively, convergent synthesis involves the preparation of multiple functionalized fragments, which are eventually assembled into the precursor and/or the final NPs. 28–31…”

Toward an Improved Triterpene 3-O-Glucuronidation: The Systematic Determination of the Relative Reactivities of Glucuronyl Donors and Acceptors

“…3 The promising potentialities of 3-O-β-glucuronide triterpenes have induced research interests in the structure and activity relationship of natural saponins and their synthetic analogues. 4 Thus, developing synthetic approaches toward 3-O-β-glucuronide triterpenes has become imperative to expand the structural diversity and explore more possibilities for clinical use.…”