Journal
ORGANIC LETTERS
Volume 7, Issue 18, Pages 3989-3992Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol051483k
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A stereocontrolled total synthesis of (+)-longicin, a representative of the class of mono-THF-acetogenins, is described. The strategy involves the utilization of D- and L-glutamic acids as chirons that correspond to two five-carbon segments harboring stereogenic centers at C4 and at C17 of the C-32 polyketide-derived natural product. The use of Grubbs' RCM reaction as a novel chain elongation strategy for the synthesis of acetogenin-type structures and a new protocol for butenolide incorporation are also described.
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