Expedient total synthesis of pyrrothine natural products and analogs

Thomas Hjelmgaard; Michael Givskov; John Nielsen

doi:10.1039/b616411k

Expedient total synthesis of pyrrothine natural products and analogs

Thomas Hjelmgaard, Michael Givskov, John Nielsen

21 Citations (Scopus)

Abstract

This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate (6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of , and (7 steps, 11-12% overall).

Original language	English
Journal	Organic & Biomolecular Chemistry
Volume	5
Issue number	2
Pages (from-to)	344-8
Number of pages	4
ISSN	1477-0520
DOIs	https://doi.org/10.1039/b616411k
Publication status	Published - 2006
Externally published	Yes

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title = "Expedient total synthesis of pyrrothine natural products and analogs",

abstract = "This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate (6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of , and (7 steps, 11-12% overall).",

author = "Thomas Hjelmgaard and Michael Givskov and John Nielsen",

note = "Keywords: Anti-Bacterial Agents; Chemistry, Organic; Chromatography, Thin Layer; DNA-Directed RNA Polymerases; Lactams; Models, Chemical; Pseudomonas; RNA, Bacterial; Streptomyces; Xenorhabdus",

year = "2006",

doi = "10.1039/b616411k",

language = "English",

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pages = "344--8",

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publisher = "Royal Society of Chemistry",

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T1 - Expedient total synthesis of pyrrothine natural products and analogs

AU - Hjelmgaard, Thomas

AU - Givskov, Michael

AU - Nielsen, John

N1 - Keywords: Anti-Bacterial Agents; Chemistry, Organic; Chromatography, Thin Layer; DNA-Directed RNA Polymerases; Lactams; Models, Chemical; Pseudomonas; RNA, Bacterial; Streptomyces; Xenorhabdus

PY - 2006

Y1 - 2006

N2 - This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate (6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of , and (7 steps, 11-12% overall).

AB - This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate (6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of , and (7 steps, 11-12% overall).

U2 - 10.1039/b616411k

DO - 10.1039/b616411k

M3 - Journal article

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SN - 1477-0520

VL - 5

SP - 344

EP - 348

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 2

ER -

Expedient total synthesis of pyrrothine natural products and analogs

Abstract

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