Organometallic enantiomeric scaffolding: organometallic chirons. Total synthesis of (-)-Bao Gong Teng A by a molybdenum-mediated [5 + 2] cycloaddition.
Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyridinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.
Zhang
Yongqiang
Y
Sanford S. Atwood Chemistry Center, Emory University, Atlanta, Georgia 30322, USA.
Liebeskind
Lanny S
LS
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003500:Cyclization; D008982:Molybdenum / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009942:Organometallic Compounds; D014326:Tropanes; C027863:bao gong teng A; D008982:Molybdenum