Concise Total Synthesis of Peyssonnoside A

Chesnokov, Gleb A; Gademann, Karl

doi:10.1021/jacs.1c07135

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Concise Total Synthesis of Peyssonnoside A

Chesnokov, Gleb A; Gademann, Karl (2021). Concise Total Synthesis of Peyssonnoside A. Journal of the American Chemical Society, 143(35):14083-14088.

Abstract

Peyssonnoside A is a marine-derived sulfated diterpenoid glucoside with a unique 5/6/3/6 tetracyclic skeleton with a highly substituted cyclopropane ring deeply embedded into the structure. Herein, we report the first total synthesis of this natural product in a concise, efficient, scalable, and highly diastereoselective fashion. The aglucone peyssonnosol was synthesized in 21% overall yield after 15 steps, featuring a Simmons–Smith cyclopropanation and Mukaiyama hydration, fully controlled by the spatial structure of the substrates.

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Item Type:	Journal Article, refereed, original work
Communities & Collections:	07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:	540 Chemistry
Scopus Subject Areas:	Physical Sciences > Catalysis Physical Sciences > General Chemistry Life Sciences > Biochemistry Physical Sciences > Colloid and Surface Chemistry
Uncontrolled Keywords:	Colloid and Surface Chemistry, Biochemistry, General Chemistry, Catalysis
Language:	English
Date:	8 September 2021
Deposited On:	17 Jan 2022 16:17
Last Modified:	18 Jan 2022 21:02
Publisher:	American Chemical Society (ACS)
ISSN:	0002-7863
OA Status:	Hybrid
Free access at:	Publisher DOI. An embargo period may apply.
Publisher DOI:	https://doi.org/10.1021/jacs.1c07135
Project Information:	: FunderSNSF : Grant ID200021_182043 : Project TitleMechanism-Based Design, Synthesis, Biological Evaluation, and Delivery of Next-Generation Antibiotics