title: Total synthesis of phorboxazole B.
abstract: An efficient and highly convergent total synthesis of the potent antitumor agent phorboxazole B has been achieved. The synthetic strategy of this synthesis features: 1) a highly efficient substrate-controlled hydrogenation to construct the functionalized cis-tetrahydropyrane unit; 2) iterative crotyl addition to synthesize the segment that contains alternating hydroxyl and methyl substituents; 3) Hg(OAc)2/I2-induced cyclization to establish the cis-tetrahydropyrane moiety; 4) 1,3-asymmetric induction in the Mukaiyama aldol reaction to afford the stereogenic centers at C9 and C3; and 5) the exploration of the Still-Gennari olefination reaction to complete the macrolide ring of phorboxazoloe B.
authors.affiliation: Shanghai Institute of Organic Chemistry, 354 Fenglin Rd, Shanghai 200032, PR China.
authors.forename: De-Run
authors.initials: DR
authors.lastname: Li
authors.forename: Dong-Hui
authors.initials: DH
authors.lastname: Zhang
authors.forename: Cai-Yun
authors.initials: CY
authors.lastname: Sun
authors.forename: Ji-Wen
authors.initials: JW
authors.lastname: Zhang
authors.forename: Li
authors.initials: L
authors.lastname: Yang
authors.forename: Jian
authors.initials: J
authors.lastname: Chen
authors.forename: Bo
authors.initials: B
authors.lastname: Liu
authors.forename: Ce
authors.initials: C
authors.lastname: Su
authors.forename: Wei-Shan
authors.initials: WS
authors.lastname: Zhou
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*
chemical_list: D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; C408887:phorboxazole A