Total synthesis of stephanotic acid methyl ester

D J  Bentley; A M Z  Slawin; C J  Moody

doi:10.1021/ol060153c

Total synthesis of stephanotic acid methyl ester

D J Bentley, A M Z Slawin, C J Moody

Research output: Contribution to journal › Article › peer-review

Abstract

The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual beta-substituted alpha-amino acid with a tryptophan C-6 to leucine beta-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.

Original language	English
Pages (from-to)	1975-1978
Number of pages	4
Journal	Organic Letters
Volume	8
DOIs	https://doi.org/10.1021/ol060153c
Publication status	Published - 11 May 2006

Keywords

ENANTIOSELECTIVE HYDROGENATION REACTIONS
ANTIMITOTIC BICYCLIC PEPTIDES
CENTRAL TRYPTOPHAN RESIDUE
CELOSIA-ARGENTEA
AMINO-ACIDS
ASYMMETRIC-SYNTHESIS
LAPORTEA-MOROIDES
CYCLIC PEPTIDE
SEEDS
DERIVATIVES

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10.1021/ol060153c

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title = "Total synthesis of stephanotic acid methyl ester",

abstract = "The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual beta-substituted alpha-amino acid with a tryptophan C-6 to leucine beta-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.",

keywords = "ENANTIOSELECTIVE HYDROGENATION REACTIONS, ANTIMITOTIC BICYCLIC PEPTIDES, CENTRAL TRYPTOPHAN RESIDUE, CELOSIA-ARGENTEA, AMINO-ACIDS, ASYMMETRIC-SYNTHESIS, LAPORTEA-MOROIDES, CYCLIC PEPTIDE, SEEDS, DERIVATIVES",

author = "Bentley, \{D J\} and Slawin, \{A M Z\} and Moody, \{C J\}",

year = "2006",

month = may,

day = "11",

doi = "10.1021/ol060153c",

language = "English",

volume = "8",

pages = "1975--1978",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

}

TY - JOUR

T1 - Total synthesis of stephanotic acid methyl ester

AU - Bentley, D J

AU - Slawin, A M Z

AU - Moody, C J

PY - 2006/5/11

Y1 - 2006/5/11

N2 - The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual beta-substituted alpha-amino acid with a tryptophan C-6 to leucine beta-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.

AB - The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual beta-substituted alpha-amino acid with a tryptophan C-6 to leucine beta-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.

KW - ENANTIOSELECTIVE HYDROGENATION REACTIONS

KW - ANTIMITOTIC BICYCLIC PEPTIDES

KW - CENTRAL TRYPTOPHAN RESIDUE

KW - CELOSIA-ARGENTEA

KW - AMINO-ACIDS

KW - ASYMMETRIC-SYNTHESIS

KW - LAPORTEA-MOROIDES

KW - CYCLIC PEPTIDE

KW - SEEDS

KW - DERIVATIVES

UR - https://www.scopus.com/pages/publications/33744749244

U2 - 10.1021/ol060153c

DO - 10.1021/ol060153c

M3 - Article

SN - 1523-7060

VL - 8

SP - 1975

EP - 1978

JO - Organic Letters

JF - Organic Letters

ER -

Total synthesis of stephanotic acid methyl ester

Abstract

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