A Convergent Synthesis of the Triterpene Saponin Asiaticoside. Issue 9 (10th May 2017)

• Record Type: Journal Article
• Authors: Shao, Wenbo; Cao, Xin; Shen, Lei; Zhang, Fuyi; Yu, Biao
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 9(2017)
• Page Start: 1270
• Page End: 1276
• Publication Date: 2017-05-10
• Subjects: glycosylation -- gold -- natural products -- total synthesis -- triterpenes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700153
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Asiaticoside (1 ), namely, 2α, 3β, 23‐trihydroxy‐urs‐12‐en‐28‐oic‐ O ‐α‐l ‐rhamnopyranosyl‐(1→4)‐β‐d ‐glucopyranosyl‐(1→6)‐β‐d ‐glucopyranoside, the major active biomarker of the traditional medicinal plant Centella asiatica, has been synthesized for the first time. The strategy features a late‐stage gold(I)‐catalyzed glycosidic condensation of a triterpenoid acid and a trisaccharide ortho ‐hexynylbenzoate. The overall preparation required a total 31 steps with the longest linear sequence occurring over 14 steps in a 6 % overall yield and starting from ursolic acid (3β‐hydroxy‐urs‐12‐en‐28‐oic acid). Abstract : Ah, sugar sugar ! Asiaticoside, the major active biomarker of the traditional medicinal plant Centella asiatica, was synthesized in a convergent linear sequence over 14 steps in 6 % overall yield by starting from ursolic acid.