Abstract
Comprehensive SummaryLuzonicosides A (1) and D (2) are the major saponins isolated from pacific starfish Echinaster Luzonicus, featuring a sterically congested 16‐membered ring which is formed by bridging the C3 and C6 of a 3β,6β‐dihydroxy‐Δ7‐ene steroid with a 1,2‐trans‐linked linear trisaccharide via glycosidic and ether bonds, respectively. Here, we describe a formal total synthesis of starfish cyclic steroid glycosides 1 and 2. The synthetic route is highly modular and versatile, involving construction of the 16‐membered macrocycles via Au(I)‐catalyzed intramolecular glycosylation, highly efficient installation of unsaturated sugar moieties with ortho‐hexynylbenzoates, elaboration of glucuronic acid unit via post‐oxidation, and a de novo synthesis of the ether‐linked pyranose unit.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: 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.