By Knolker, Hans-Joachim
For greater than 60 years, The Alkaloids has been the major ebook sequence within the box of alkaloid chemistry. in additional than 70 volumes all elements of alkaloids, together with chemistry, biology and pharmacology, were lined in top of the range undying experiences written through popular specialists within the field.
- The Alkaloids is the best e-book sequence within the box of alkaloid chemistry.
- In greater than 70 volumes all points of alkaloids, together with chemistry, biology and pharmacology, were covered.
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131 Reduction of the ketone (þ)-228 formed in this way with sodium borohydride mediated by cerium trichloride gave the (R)-alcohol (À)-229 as an inseparable mixture of diastereomers (91:9). 130 Reagents and conditions: (a) BnO(CH2)4MgBr, THF, 0 C to rt, 2 h; (b) MsCl, py, DMAP, 0 C, 12 h; (c) BnNH2 (neat), 80 C, 2 days, then ﬂash chromatography; (d) H2 (1 atm), Pd(OH)2/C, MeOH, rt, 2 days, then Pd/C, 4 days; (e) CCl4, PPh3, NEt3, CH2Cl2, rt, 12 h; (f) Bu4NF, THF, rt, overnight. 5 h; (b) CeCl3$7H2O, MeOH, rt, 1 h, then NaBH4, À78 C, 20 min; (c) MsCl, NEt3, CH2Cl2, 0 C, 45 min; (d) NaN3, DMF, 80 C, 4 h; (e) TFA, CH2Cl2eH2O (10:1), rt, 15 h; (f) H2 (1 atm), Pd(OH)2/C, EtOH, rt, 12 h; (g) TBSOTf, py, DMF, 0 C, 1 h; (h) H2 (1 atm), Pd/C, EtOAc, rt, 2 h; (i) NaH, THF, 0 C to rt, 2 h; (j) conc.
Alkaloids. Several synthetic epimers have also been reported (Figure 7). They include (Æ)-1-epi-lentiginosine (rac-129)87; (À)-1-epi-lentiginosine (ent129),88e90 which is also known as (À)-2,8a-di-epi-lentiginosine; (À)-8aepi-lentiginosine (130)85,91,92; (þ)-8a-epi-lentiginosine (ent-130),90,93,94 which is equivalent to (þ)-1,2-di-epi-lentiginosine; and (þ)-1,8a-di-epilentiginosine,95 which is actually the (þ)-enantiomer of 2-epi-lentiginosine (ent-128). Syntheses of these synthetic epimers will not be described unless they happen to be formed along with the natural products or their H OH H OH N N 129 OH N 128 127 H OH OH H OH OH N OH (–)-130 Figure 7 (þ)-Lentiginosine (127), (À)-2-epi-lentiginosine (128) and synthetic epimers.
HCl (1 M)eMeCN (1:1), rt, 20 min, then NaHCO3; (e) LiAlH4, Et2O, 0 C, 2 h; (f) Ti(OiPr)4, (þ)-DIPT, 4 Å molecular sieves, CH2Cl2, À20 C, 30 min, then add tBuOOH, À20 C, 22 h; (g) p-TsCl, NEt3, CH2Cl2, rt, 3 h; (h) NaN3, DMF, 80 C, 3 h; (i) DDQ, CH2Cl2eH2O (5:1), rt, 3 h; (j) p-TsCl, py, rt, 30 min; (k) H2 (1 atm), Lindlar catalyst, MeOH, rt, 3 h, then KOH in MeOH (2 drops). 54 Joseph P. 6 Simultaneous Formation of N/C-5 and C-8/C-8a Bonds: An Aza-DielseAlder Approach The unique approach to the synthesis of both (þ)-lentiginosine (127) and its (À)-enantiomer by Shao and Yang143 featured an aza-DielseAlder reaction between the Danishefsky-type oxygenated diene 282 and the known D1pyrrolines 283 or ent-283144 derived from L- or D-tartaric acid, respectively (Scheme 39).