![(3R,4aR,7aS,9aR,10S,11R,13aR,13bS,15aS,15bR)-3,11-Dihydroxy-10-(hydroxymethyl)-4,4,7a,10,13a,15b-hexamethyl-1,2,3,4,4a,7,7a,8,9,9a,10,11,12,13,13a,13b,14,15,15a,15b-icosahydro-5H-naphtho[2',1':4,5]cyc
lohepta[1,2-a]naphthalen-5-one structure](https://static.chemtradehub.com/structs/538/53800-21-8-9f18.webp "(3R,4aR,7aS,9aR,10S,11R,13aR,13bS,15aS,15bR)-3,11-Dihydroxy-10-(hydroxymethyl)-4,4,7a,10,13a,15b-hexamethyl-1,2,3,4,4a,7,7a,8,9,9a,10,11,12,13,13a,13b,14,15,15a,15b-icosahydro-5H-naphtho[2',1':4,5]cyc
lohepta[1,2-a]naphthalen-5-one structure")
Gram-scale synthesis of alstoscholarinoid B via a bio-inspired strategy
Literature Information
Publication Date
2023-10-26
DOI
10.1039/D3OB01625K
Impact Factor
3.876
Authors
Long He, Wenting Zhang, Xiaocheng Zhang, Xiaohui Wu, Yimeng Han, Jiahang Yan
View Original
Abstract
Alstoscholarinoid A is a novel rearranged triterpene with an unprecedented 6/6/5/6/6/6 framework and an additional unique C28 → C11-olide F-ring, and displays antihyperuricemic bioactivity. Herein, we report a bio-inspired synthesis of alstoscholarinoid B in a stepwise manner, which is amenable to gram-scale synthesis. The synthesis involved the Chugaev elimination as a key step to realize the migration of the Δ11,12-double bond of oleanolic acid, and also featured a sequential LiHMDS-mediated intramolecular aldol condensation/lactonization to establish the polycyclic ring system. Additionally, a tandem deprotection/aldol condensation/lactonization process under the influence of LiI/2,4,6-collidine for forging the polycyclic scaffold was also serendipitously discovered. Mechanistic studies indicated that lithium carboxylate might function as an inner base for the chemoselective α-deprotonation of the C12-aldehyde.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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4,4,5,5-Tetramethyl-2-(1-propyn-1-YL)-1,3,2-dioxaborolane
CAS Number:
347389-75-7
Molecular Formula:
C9H15BO2
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