A Versatile Intermediate for the Synthesis of Pyranoquinone Antibiotics

George A. Kraus, Jianmin Shi, Donald Reynolds

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

As a result of the sophisticated detection and isolation procedures developed by Omura1 and others, the family of biologically active pyranoquinones continues to grow rapidly. As a consequence of their interesting structures and useful activity, several synthetic approaches have already appeared.2 Its members include the antimyco-plasmal antibiotics frenolicin B (1)3 and nanaomycin A (2),4 the antifungal agent kalafungin (3),5 the antibiotics me-dermycin (4)6 and mederrhodin (5),7 and the novel C-glycoside SCH 38519 (6),8 which inhibits the growth of Gram-negative and Gram-positive microorganisms. It is clear from an examination of their structures depicted below that the primary difference lies in the substitution pattern on the naphthoquinone subunit. Since an acid such as 2 can be converted into a lactone in high yield under mild conditions,4 our interest in developing a common intermediate for the synthesis of all of these natural products led us to embark on the preparation of quinone 7, wherein X could be a phenylthio group or a bromide or chloride.

Original languageEnglish (US)
Pages (from-to)1105-1106
Number of pages2
JournalJournal of Organic Chemistry
Volume55
Issue number3
DOIs
StatePublished - Jan 1 1990

Fingerprint

Anti-Bacterial Agents
Naphthoquinones
Antifungal Agents
Lactones
Biological Products
Bromides
Microorganisms
Chlorides
Substitution reactions
Acids
nanaomycin A
frenolicin B
benzoquinone
kalafungin
C-glycoside

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A Versatile Intermediate for the Synthesis of Pyranoquinone Antibiotics. / Kraus, George A.; Shi, Jianmin; Reynolds, Donald.

In: Journal of Organic Chemistry, Vol. 55, No. 3, 01.01.1990, p. 1105-1106.

Research output: Contribution to journalArticle

Kraus, George A. ; Shi, Jianmin ; Reynolds, Donald. / A Versatile Intermediate for the Synthesis of Pyranoquinone Antibiotics. In: Journal of Organic Chemistry. 1990 ; Vol. 55, No. 3. pp. 1105-1106.
@article{705cabebfd0347ca8c2e1fd413bd03e0,
title = "A Versatile Intermediate for the Synthesis of Pyranoquinone Antibiotics",
abstract = "As a result of the sophisticated detection and isolation procedures developed by Omura1 and others, the family of biologically active pyranoquinones continues to grow rapidly. As a consequence of their interesting structures and useful activity, several synthetic approaches have already appeared.2 Its members include the antimyco-plasmal antibiotics frenolicin B (1)3 and nanaomycin A (2),4 the antifungal agent kalafungin (3),5 the antibiotics me-dermycin (4)6 and mederrhodin (5),7 and the novel C-glycoside SCH 38519 (6),8 which inhibits the growth of Gram-negative and Gram-positive microorganisms. It is clear from an examination of their structures depicted below that the primary difference lies in the substitution pattern on the naphthoquinone subunit. Since an acid such as 2 can be converted into a lactone in high yield under mild conditions,4 our interest in developing a common intermediate for the synthesis of all of these natural products led us to embark on the preparation of quinone 7, wherein X could be a phenylthio group or a bromide or chloride.",
author = "Kraus, {George A.} and Jianmin Shi and Donald Reynolds",
year = "1990",
month = "1",
day = "1",
doi = "10.1021/jo00290a056",
language = "English (US)",
volume = "55",
pages = "1105--1106",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

T1 - A Versatile Intermediate for the Synthesis of Pyranoquinone Antibiotics

AU - Kraus, George A.

AU - Shi, Jianmin

AU - Reynolds, Donald

PY - 1990/1/1

Y1 - 1990/1/1

N2 - As a result of the sophisticated detection and isolation procedures developed by Omura1 and others, the family of biologically active pyranoquinones continues to grow rapidly. As a consequence of their interesting structures and useful activity, several synthetic approaches have already appeared.2 Its members include the antimyco-plasmal antibiotics frenolicin B (1)3 and nanaomycin A (2),4 the antifungal agent kalafungin (3),5 the antibiotics me-dermycin (4)6 and mederrhodin (5),7 and the novel C-glycoside SCH 38519 (6),8 which inhibits the growth of Gram-negative and Gram-positive microorganisms. It is clear from an examination of their structures depicted below that the primary difference lies in the substitution pattern on the naphthoquinone subunit. Since an acid such as 2 can be converted into a lactone in high yield under mild conditions,4 our interest in developing a common intermediate for the synthesis of all of these natural products led us to embark on the preparation of quinone 7, wherein X could be a phenylthio group or a bromide or chloride.

AB - As a result of the sophisticated detection and isolation procedures developed by Omura1 and others, the family of biologically active pyranoquinones continues to grow rapidly. As a consequence of their interesting structures and useful activity, several synthetic approaches have already appeared.2 Its members include the antimyco-plasmal antibiotics frenolicin B (1)3 and nanaomycin A (2),4 the antifungal agent kalafungin (3),5 the antibiotics me-dermycin (4)6 and mederrhodin (5),7 and the novel C-glycoside SCH 38519 (6),8 which inhibits the growth of Gram-negative and Gram-positive microorganisms. It is clear from an examination of their structures depicted below that the primary difference lies in the substitution pattern on the naphthoquinone subunit. Since an acid such as 2 can be converted into a lactone in high yield under mild conditions,4 our interest in developing a common intermediate for the synthesis of all of these natural products led us to embark on the preparation of quinone 7, wherein X could be a phenylthio group or a bromide or chloride.

UR - http://www.scopus.com/inward/record.url?scp=0025355160&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025355160&partnerID=8YFLogxK

U2 - 10.1021/jo00290a056

DO - 10.1021/jo00290a056

M3 - Article

VL - 55

SP - 1105

EP - 1106

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 3

ER -