Organic Letters p. 1975 - 1978 (2006)
Update date:2022-08-04
Topics:
Bentley, David J.
Slawin, Alexandra M. Z.
Moody, Christopher J.
The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual β-substituted α-amino acid with a tryptophan C-6 to leucine β-carbon link, has been synthesized. The key steps include the formation of this amino acid through a thioxo-oxazolidine intermediate and a Horner-Wadsworth-Emmons reaction using a phosphonoglycine, derived by a dirhodium(II)-catalyzed N-H insertion reaction, to give a dehydroamino acid and subsequent rhodium(I)-catalyzed asymmetric hydrogenation to introduce the modified tryptophan residue.
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(2003)Doi:10.1248/cpb.24.1514
(1976)Doi:10.1016/j.bmcl.2006.03.082
(2006)Doi:10.1002/jps.2600700837
(1981)Doi:10.1016/S0040-4039(00)74594-1
(1976)