1. Organic Synthesis
Michael Smith
Chapter 12
Carey & Sundberg Chapter 8

26. ref

27. ref

32. HPdX species. The generation of this species by the oxidative addition of HX to a palladium(O) complex is known for strong acids such as HCl, but such a catalyst fails to effect cyclization. The contrast between palladium chloride, which fails to serve as a catalyst, and palladium acetate, which does serve as acatalyst, led us to consider the feasibility of employing a simple carboxylic acid even though an oxidative addition of acetic acid was unknown,

34. ref
Heck reaction

35. ref

38. ref

39. ref

40. ref

42. Nature 2007, 450, 243

46. J. Am. Chem. Soc. 119, 10302–10316 (1997)

51. Danheiser Annulation

64. Tetrahedron 63 (2007) 4310–4318

66. Total Synthesis of (+)-b-Erythroidine

67. Scheme 2. Preparation of amino acid fragment 18
Scheme 2. Preparation of amino acid fragment 18. Reagents and conditions: a) Ag2O, TsCl, KI, CH2Cl2; b) Tf2O, Et3N, CH2Cl2, 15 8C; c) nBuLi, CHCCH2OTHP, THF/DMPU, 208C; d) NaI, DMF, 708C; e) Zn, AcOH, EtOH, sonication; f) MeI, Ag2O, Et2O; g) PPTS, MeOH; h) NaH2Al(OCH2CH2OMe)2, Et2O, 08C, then I2 ; i) CHCTMS, [Pd-
ACHTUNGTRENUNG(PPh3)2Cl2], CuI, iPr2NH, THF, sonication; j) K2CO3, MeOH; k) mCPBA, NaHCO3, CH2 Cl2, 50 8C; l) Cl3CCN, DBU, 4 G M.S., CH2Cl2, 08C; m) BF3·OEt2, CH2Cl2, 20 8C; n) 1m HCl, THF, then Boc2O, NaHCO3 ; o) NaIO4, THF/H2O; p) NaClO2, NaH2PO4, 2-methyl-2-butene, tBuOH/ H2O; q) CH2N2, MeOH; r) TFA, CH2Cl2.

68. Scheme 3. a) MeO2C (CH2)2CHO, NaBH(OAc)3, 4 A M. S
Scheme 3. a) MeO2C (CH2)2CHO, NaBH(OAc)3, 4 A M.S., THF, 0oC; b) allyl bromide, K2CO3, DMF; c) NaH, MeOH, toluene, reflux; d) NaH, THF, 0oC, then AlH3, -10 oC; e) BrCH2COCl, pyridine, CH2Cl2, 0oC; f) SmI2, THF; g) SOCl2, pyridine; h) 10% NaOH, dioxane, reflux, then acidified with conc. HCl; i) 30 (0.1 equiv), CH2Cl2.

69. Nature 2008, 456, 933