Synthesis and absolute stereochemistry of roseophilin.
The enantiospecific total synthesis of natural roseophilin has been completed in 7.0% overall yield over 15 steps by means of an asymmetric cyclopentannelation. This establishes the absolute configuration of the natural product as 22R,23R. Cyclopentenone (+)-12 was prepared in 78% yield and 86% ee in the key step.
Harrington
P E
PE
Department of Chemistry, 2545 The Mall, University of Hawaii, Honolulu, HI 96822, USA.
Tius
M A
MA
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