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- Title
Stereoselective Total Synthesis of Pyranicin and 4‐Epi‐Pyranicin from Carbohydrate Precursors.
- Authors
Ambati, Praveen; Gupta, Akanksha; Bandi, Anjaneyulu; Perali, Ramu Sridhar
- Abstract
Herein, we describe a simple and efficient pathway for the total synthesis of pyranicin and 4‐epi‐pyranicin by utilizing carbohydrates as chiral raw materials for the first time. The general synthetic strategy involves the formation of two main fragments: Fragment 1 is the central tetrahydropyran core, which was constructed in a total of 10 steps from 2,3,4,6‐tetra‐O‐acetyl D‐glucal via Ferrier‐type rearrangement and oxidative cyclization as the key steps. Fragment 2 is the butenolide fragment, which was obtained in a gram scale with a total of 14 steps from diacetyl‐L‐rhamnal involving a ring contraction strategy.
- Subjects
RAW materials; RING formation (Chemistry); NATURAL products
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 22, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400244