NEW APPROACHES TO THE SYNTHESIS OF SPERMINE AND SPERMIDINE ALKALOIDS
New approaches to the formation of macrocyclic lactams are described involving successive ring expansion of 8-lactams and other heterocyclic systems.These methods have been used in the synthesis of a number of spermine and spermidine alkaloids including homaline, celacinnine, dihydroperiphylline, chaenorhine and verbascenine.
Wasserman, Harry H.,Robinson, Ralph P.
p. 279 - 288
(2007/10/02)
THE USE OF β-LACTAMS IN THE SYNTHESIS OF SPERMINE AND SPERMIDINE ALKALOIDS. TOTAL SYNTHESIS OF HOMALINE
The optically active plant product homaline (6) has been synthesized in a convergent sequence starting with β-phenyl-β-alanine and putrescine (14).The key transformation in this sequence is the ring expansion by transamidation of a functionalized chiral β-lactam precursor.
Wasserman, Harry H.,Berger, Gregory D.
p. 2459 - 2464
(2007/10/02)
TRANSAMIDATION REACTIONS USING β-LACTAMS. THE SYNTHESIS OF HOMALINE
The synthesis of the plant product, homaline, by a translactamization process involving the β-lactam, (-)-4-phenyl-2-azetidinone, is described.
Wasserman, Harry H.,Berger, Gregory D.,Cho, Kathleen R.
p. 465 - 468
(2007/10/02)
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