title: Stereoselective synthesis of the C1-C29 part of amphidinol 3.
abstract: Stereoselective synthesis of the C1-C29 part of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asymmetric reduction to form the C9-C10 and C14-C15 bonds, respectively. The C21-C29 part was synthesized via successive cross metathesis and oxa-Michael addition sequence to construct the 1,3-diol system at C25 and C27 and Brown asymmetric crotylation to introduce the stereogenic centers at C23 and C24. Coupling of the C1-C20 and C21-C29 parts was achieved by Julia-Kocienski olefination and regio- and stereoselective dihydroxylation of the C20-C21 double bond in the presence of the C4-C5 and C8-C9 double bonds to afford the C1-C29 part of AM3.
authors.affiliation: Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University , 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Tsuruda
authors.forename: Makoto
authors.initials: M
authors.lastname: Ebine
authors.forename: Aya
authors.initials: A
authors.lastname: Umeda
authors.forename: Tohru
authors.initials: T
authors.lastname: Oishi
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008094:Lithium / Q000737:chemistry; D018942:Macrolides / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095722:Amphidinols
chemical_list: D000475:Alkenes; D008094:Lithium; D018942:Macrolides; D011714:Pyrans; C438973:amphidinol 3; D000095722:Amphidinols