Ester-Imine Condensations: Preparation of Racemic Intermediates for the Synthesis of the Carbapenem Antibiotics PS-5 and PS-6

Deok Chan Ha; David J. Hart

doi:10.7164/antibiotics.40.309

Ester-Imine Condensations: Preparation of Racemic Intermediates for the Synthesis of the Carbapenem Antibiotics PS-5 and PS-6

Deok Chan Ha, David J. Hart

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

15 Citations (Scopus)

Abstract

The lithium enolates of ethyl butyrate (7) and ethyl isovalerate (19) react with N-p-methoxyphenylcinnamaldimine (8) in tetrahydrofuran (THF) - hexamethylphosphoric triamide (HMPA) to afford predominantly trans β-lactams 9 (67 %) and 20 (78 %), respectively. β-Lactam 9 was converted to PS-5 (5) intermediate 18 in 21 % overall yield (8 steps). β-Lactam 20 was converted to PS-6 (6) analog 28 in 22 % overall yield using an eight step sequence.

Original language	English
Pages (from-to)	309-319
Number of pages	11
Journal	The Journal of antibiotics
Volume	40
Issue number	3
DOIs	https://doi.org/10.7164/antibiotics.40.309
Publication status	Published - 1987
Externally published	Yes

ASJC Scopus subject areas

Pharmacology
Drug Discovery

Access to Document

10.7164/antibiotics.40.309

Cite this

@article{ca45452f9b984ca58bb9bc338991a0c9,

title = "Ester-Imine Condensations: Preparation of Racemic Intermediates for the Synthesis of the Carbapenem Antibiotics PS-5 and PS-6",

abstract = "The lithium enolates of ethyl butyrate (7) and ethyl isovalerate (19) react with N-p-methoxyphenylcinnamaldimine (8) in tetrahydrofuran (THF) - hexamethylphosphoric triamide (HMPA) to afford predominantly trans β-lactams 9 (67 %) and 20 (78 %), respectively. β-Lactam 9 was converted to PS-5 (5) intermediate 18 in 21 % overall yield (8 steps). β-Lactam 20 was converted to PS-6 (6) analog 28 in 22 % overall yield using an eight step sequence.",

author = "Ha, {Deok Chan} and Hart, {David J.}",

year = "1987",

doi = "10.7164/antibiotics.40.309",

language = "English",

volume = "40",

pages = "309--319",

journal = "The Journal of antibiotics",

issn = "0021-8820",

publisher = "Japan Antibiotics Research Association",

number = "3",

}

TY - JOUR

T1 - Ester-Imine Condensations

T2 - Preparation of Racemic Intermediates for the Synthesis of the Carbapenem Antibiotics PS-5 and PS-6

AU - Ha, Deok Chan

AU - Hart, David J.

PY - 1987

Y1 - 1987

N2 - The lithium enolates of ethyl butyrate (7) and ethyl isovalerate (19) react with N-p-methoxyphenylcinnamaldimine (8) in tetrahydrofuran (THF) - hexamethylphosphoric triamide (HMPA) to afford predominantly trans β-lactams 9 (67 %) and 20 (78 %), respectively. β-Lactam 9 was converted to PS-5 (5) intermediate 18 in 21 % overall yield (8 steps). β-Lactam 20 was converted to PS-6 (6) analog 28 in 22 % overall yield using an eight step sequence.

AB - The lithium enolates of ethyl butyrate (7) and ethyl isovalerate (19) react with N-p-methoxyphenylcinnamaldimine (8) in tetrahydrofuran (THF) - hexamethylphosphoric triamide (HMPA) to afford predominantly trans β-lactams 9 (67 %) and 20 (78 %), respectively. β-Lactam 9 was converted to PS-5 (5) intermediate 18 in 21 % overall yield (8 steps). β-Lactam 20 was converted to PS-6 (6) analog 28 in 22 % overall yield using an eight step sequence.

UR - http://www.scopus.com/inward/record.url?scp=0023113036&partnerID=8YFLogxK

U2 - 10.7164/antibiotics.40.309

DO - 10.7164/antibiotics.40.309

M3 - Article

C2 - 3570984

AN - SCOPUS:0023113036

SN - 0021-8820

VL - 40

SP - 309

EP - 319

JO - The Journal of antibiotics

JF - The Journal of antibiotics

IS - 3

ER -

Ester-Imine Condensations: Preparation of Racemic Intermediates for the Synthesis of the Carbapenem Antibiotics PS-5 and PS-6

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this