title: Synthesis and configuration of the nonadecenetriol isolated from seeds of Persea americana.
abstract: In an effort to establish the relative as well as absolute configuration of the trypanocidally active natural nonadec-6-en-1,2,4-triol isolated from Persea americana, the (2S,4R), (2S,4S), and (2R,4R) isomers were synthesized. The stereogenic centers taken from enantiopure chiral epoxy building blocks derived from inexpensive and readily available D-glucolactone. The (2R,4R) isomer gave (1)H and (13)C NMR as well as specific rotation in excellent consistence with those reported for the natural triol.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Yan
authors.forename: Shao-Min
authors.initials: SM
authors.lastname: Zhang
authors.forename: Yikang
authors.initials: Y
authors.lastname: Wu
authors.forename: Po
authors.initials: P
authors.lastname: Gao
mesh_terms: D005233:Fatty Alcohols / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D027421:Persea / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; C568942:nonadec-6-en-1,2,4-triol