Enantioselective total synthesis of (R)-(−)-complanine

• Krystal A. D. Kamanos and
• Jonathan M. Withey

Beilstein J. Org. Chem. 2012, 8, 1695–1699, doi:10.3762/bjoc.8.192

• the obscuraminols [2]. Such synthetic studies are currently underway in our laboratory. Experimental Undeca-5,8-diyn-1-ol (2): To a suspension of anyhydrous Cs2CO3 (9.19 g, 28.2 mmol), TBAI (10.39 g, 28.2 mmol) and CuI (5.37 g, 28.2 mmol) in anhydrous DMF (60 mL) was added 5-hexyn-1-ol (3.11 mL, 28.2

• . Retrosynthetic analysis of (R)-(−)-complanine. Reagents and conditions: (a) Cs2CO3, CuI, TBAI, DMF, rt, 24 h, 91%; (b) H2 (1 atm), Lindlar catalyst, EtOAc, pyridine, rt, 24 h; (c) DMSO, (COCl)2, DCM, −78 °C, then; 1, −78 °C, 45 min, then, Et3N, 0 °C, 1.5 h, 86% from 2. Direct approach to amino alcohol 4

Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica

• Lu Zou,
• Ruixiang Blake Zheng and
• Todd L. Lowary

Beilstein J. Org. Chem. 2012, 8, 1219–1226, doi:10.3762/bjoc.8.136

• ) TBDPSCl, imidazole, DMF, 78%; (b) BnBr, NaH, TBAI, 84%; (c) TBAF, THF, 83%; (d) CH3I, NaH, DMF, 87%; (e) HO-P(O)(OBn)2, NIS, AgOTf, CH2Cl2, 70%; (f) H2, Pd(OH)2–C, NaHCO3, CH3OH, 91%. Reagents and conditions: (a) Ag2O, CaSO4, CH3I, 52%; (b) Ac2O–HOAc–H2SO4, 70:30:1, 96%; (c) EtSH, BF3·OEt2, CH2Cl2, 75