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Total Synthesis of Starfish Cyclic Steroid Glycosides. Part 3, Formal Total Synthesis of Luzonicosides A and D.

  • Published In: Chinese Journal of Chemistry, 2023, v. 41, n. 8. P. 903 1 of 3

  • Database: Academic Search Ultimate 2 of 3

  • Authored By: Zhu, Dapeng; Geng, Mingyu; Shen, Dacheng; Yu, Biao 3 of 3

Abstract

Comprehensive Summary: Luzonicosides 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. [ABSTRACT FROM AUTHOR]

Additional Information

  • Source:Chinese Journal of Chemistry. 2023/04, Vol. 41, Issue 8, p903
  • Document Type:Article
  • Subject Area:Zoology
  • Publication Date:2023
  • ISSN:1001-604X
  • DOI:10.1002/cjoc.202200787
  • Accession Number:162434183
  • Copyright Statement:Copyright of Chinese Journal of Chemistry is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

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