Abstract
The proposed biosynthetic pathways to ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share a dramatic epoxide-opening cascade as a key step. Polycyclic structures generated in these biosynthetic pathways display biological effects ranging from potentially therapeutic properties to extreme lethality. Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades. In this review we summarize how such epoxide-opening cascade reactions have been used in the synthesis of ladder polyethers and oxasqualenoid natural products.
Highlights
Marine polyether natural products, polycyclic molecules of marine origin with regular occurrence of multiple C-O-C motifs, include the distinct families of the ladder polyethers and the oxasqualenoids.Members in both of these families exhibit biological activities ranging from potentially therapeutic properties to extreme lethality
Much of the structural complexity of ladder polyether and oxasqualenoid natural products can be traced to these hypothesized cascades
Our discussions on oxasqualenoid natural products, will be limited to natural products from this family that resemble ladder polyethers and feature multiple fused rings; that is, to those members of the family that are proposed to originate from biosynthetic cascades with multiple endo-selective epoxide-opening steps
Summary
Polycyclic molecules of marine origin with regular occurrence of multiple C-O-C motifs, include the distinct families of the ladder polyethers and the oxasqualenoids Members in both of these families exhibit biological activities ranging from potentially therapeutic properties to extreme lethality. The proposed biosynthetic pathways to both ladder polyethers of polyketide origin and oxasqualenoids of terpenoid origin share dramatic epoxide-opening cascades as key steps [1,2] These reactions are postulated to be involved in the biogenesis of polyethers, and could be utilized as a method to rapidly construct the molecular frameworks in these natural products [3]. A further distinction is made between the approaches developed for control of regioselectivity in epoxide-opening reactions, i.e., those that rely on electronically biased epoxides and those in which the epoxides may be considered to be electronically unbiased
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
