Stereoselective Substrate-Controlled Asymmetric Syntheses of both 2,5-cis- and 2,5-trans-Tetrahydrofuranoid Oxylipids: Stereodivergent Intramolecular Amide Enolate Alkylation.
The concise, highly stereoselective, substrate-controlled asymmetric total syntheses of both 2,5-cis- and 2,5-trans-tetrahydrofuranoid nematocidal oxylipids from the Australian brown algae Notheia anomala have been accomplished in a stereodivergent fashion. The highly stereoselective intramolecular amide enolate alkylation strategy provides access to both stereoisomers of the 3-hydroxy-2,5-disubstituted tetrahydrofuran core of these marine natural products through chelate and nonchelate control, which is driven by the C3-hydroxy protecting group. This approach offers an optional and highly stereoelective access to any of the eight possible stereoisomers of the 2,5-disubstituted-3-oxygenated tetrahydrofuran skeleton, an important structural feature which is present in many biologically active natural products.
College of Pharmacy, Ajou University, Suwon, 16499, Korea.
Hongjun
0000-0003-2996-9870
H
Jang
College of Pharmacy, Ajou University, Suwon, 16499, Korea.
Iljin
0000-0003-1248-5757
I
Shin
College of Pharmacy, Ajou University, Suwon, 16499, Korea.
Dongjoo
0000-0002-6337-2229
D
Lee
College of Pharmacy, Ajou University, Suwon, 16499, Korea. hkimajou@ajou.ac.kr.
Hyoungsu
0000-0002-2774-8727
H
Kim
College of Pharmacy, Seoul National University, Seoul, 08826, Korea.
Deukjoon
0000-0003-4079-8734
D
Kim
alkylations; cyclizations; heterocycles; natural products; total synthesis