Biomimetic asymmetric total synthesis of (-)-laurefucin via an organoselenium-mediated intramolecular hydroxyetherification.
The first asymmetric total synthesis of (-)-laurefucin (1), a unique C-15 acetogenin with a 2,8-dioxabicyclo[5.2.1]decane skeleton, has been accomplished in nine steps in 31% overall yield from known oxocene 10. Highlights of the highly stereoselective synthesis include a novel organoselenium-mediated biomimetic hydroxyetherification.
Kim
Byungsook
B
The Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
Lee
Miseon
M
Kim
Mi Jung
MJ
Lee
Hyunjoo
H
Kim
Sanghee
S
Kim
Deukjoon
D
Koh
Minseob
M
Park
Seung Bum
SB
Shin
Kye Jung
KJ
D032701:Biomimetics; D004987:Ethers / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D016566:Organoselenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D004987:Ethers; D005663:Furans; D016566:Organoselenium Compounds; C017459:laurefucin