Stereoselective Total Synthesis of Pyranicin and 4‐Epi‐Pyranicin from Carbohydrate Precursors

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 co...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-06, Vol.27 (22), p.n/a
Main Authors: Ambati, Praveen, Gupta, Akanksha, Bandi, Anjaneyulu, Perali, Ramu Sridhar
Format: Article
Language:English
Subjects:
acetogenins
Carbohydrates
natural products
oxidative cyclization
Raw materials
Stereoselectivity
Synthesis
total synthesis
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Summary: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. The total synthesis of pyranicin and 4‐epi‐pyranicin has been accomplished from carbohydrate precursors. The general synthetic strategy includes two main fragment formations: (1) THP fragment (2) Butenolide fragment.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400244