title: Convergent and enantioselective total synthesis of (-)-amphidinolide O and (-)-amphidinolide P.
abstract: A convergent and enantioselective total synthesis of (-)-amphidinolide O (1) and P (2), 15-membered macrolides with seven chiral centers along with many functional groups, is described. The key reactions include enantioselective Brown allylation, anti- and syn-selective aldol reactions, (E)-selective olefin metathesis, conformation-controlled stereoselective epoxidation, and selective introduction of the exomethylene group. Assignments of the absolute stereochemistries of the natural (+)-amphidinolide O (ent-1) and P (ent-2) are also discussed in detail.
authors.affiliation: Department of Chemistry, Sogang University, Organic Chemistry Research Center, Shinsu-dong 1, Mapo-gu, Seoul 121-742, Korea.
authors.forename: Min-ho
authors.initials: MH
authors.lastname: Hwang
authors.forename: Seo-Jung
authors.initials: SJ
authors.lastname: Han
authors.forename: Duck-Hyung
authors.initials: DH
authors.lastname: Lee
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D000097442:Amphidinolides
chemical_list: D018942:Macrolides; C585257:amphidinolide O; D000097442:Amphidinolides; C407987:amphidinolide P