Novel "protecting group-dependent" alkylation-RCM strategy to medium-sized oxacycles: first total synthesis of --isoprelaurefucin.
[reaction: see text] A novel "protecting group-dependent" alkylation strategy was developed for complementary diastereoselective syntheses of alpha,alpha'-syn- and alpha,alpha'-anti-bis-alkenes 2 and 3, which represent ring-closing metathesis (RCM) substrates for medium-sized oxacycles. This principle has been applied to a stereoselective and concise total synthesis of (-)-isoprelaurefucin (4) in 14 steps in 12% overall yield from known epoxide 8.
Lee
Hyunjoo
H
College of Pharmacy, Seoul National University, Kwanak-Ku, Korea.
Kim
Hyoungsu
H
Yoon
Taehyun
T
Kim
Byungsook
B
Kim
Sanghee
S
Kim
Hee-Doo
HD
Kim
Deukjoon
D
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D000577:Amides / Q000737:chemistry; D003500:Cyclization; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis / Q000737:chemistry
D000475:Alkenes; D000577:Amides; D006574:Heterocyclic Compounds, 2-Ring; D010082:Oxepins; C510882:isoprelaurefucin