Enantioselective formal total synthesis of roseophilin.
[formula: see text] An enantioselective formal total synthesis of roseophilin 3 is presented. The 13-membered ring of macrotricycle 1 was formed via an efficient ring-closing metathesis reaction of bicycle 4. A palladium-catalyzed methoxycarbonylation reaction of enol triflate 5 was utilized to functionalize the right-hand ring of bicycle 2. The allyl substituent was introduced by a radical allylation of alpha-bromoketone 17.
Bamford
S J
SJ
Laboratory of Organic Chemistry, University of Amsterdam, The Netherlands.
Luker
T
T
Speckamp
W N
WN
Hiemstra
H
H
D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; C408872:roseophilin