Total synthesis of bacilosarcins A and B

Angewandte Chemie - International Edition

Volumn 48, Issue 6, 2009, Pages 1144-1148

  Enomoto, Masaru ^a   Kuwahara, Shigefumi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkaloids; Epoxidation; Heterocycles; Natural products; Total synthesis

Indexed keywords

CHEMICAL REACTIONS; CHEMICAL STABILITY; SYNTHESIS (CHEMICAL);

ALKALOIDS; EPOXIDATION; HETEROCYCLES; NATURAL PRODUCTS; TOTAL SYNTHESIS;

THERMODYNAMIC STABILITY;

ALKALOID; BACILOSARCIN A; BACILOSARCIN B; FUSED HETEROCYCLIC RINGS; HERBICIDE; MORPHOLINE DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKALOIDS; HERBICIDES; HETEROCYCLIC COMPOUNDS, 2-RING; MORPHOLINES;

EID: 59049106876     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804571     Document Type: Article

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53. 1H NMR spectrum of 29 indicated that a small degree of asymmetric induction took place in the Amadori reaction of 6·HCl, which give 29 as a 3:2 epimeric mixture, instead of a 1:1 mixture, as in the case of the model compound 25.
54. 4 and then concentrating the resulting mixture showed very good agreement with that of natural bacilosarcin B as well as with that of 2·HCl, but was significantly different from that of the free amine (see the Supporting Information).