A stereoselective synthesis of the C(3)-C(13) and C(14)-C(24) fragments of macrolactin A

Shu Kun Li; Rui Xu; Xiang Shu Xiao; Dong Lu Bai

doi:10.1002/cjoc.20000180621

A stereoselective synthesis of the C(3)-C(13) and C(14)-C(24) fragments of macrolactin A

Shu Kun Li, Rui Xu, Xiang Shu Xiao, Dong Lu Bai

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

10 Scopus citations

Abstract

Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.

Original language	English (US)
Pages (from-to)	910-923
Number of pages	14
Journal	Chinese Journal of Chemistry
Volume	18
Issue number	6
DOIs	https://doi.org/10.1002/cjoc.20000180621
State	Published - 2000
Externally published	Yes

Keywords

Antiviral
Julia olefination
Macrolactin A
Stereoselective synthesis
Sulfone alkylation
Wittig reaction

ASJC Scopus subject areas

General Chemistry

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10.1002/cjoc.20000180621

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title = "A stereoselective synthesis of the C(3)-C(13) and C(14)-C(24) fragments of macrolactin A",

abstract = "Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.",

keywords = "Antiviral, Julia olefination, Macrolactin A, Stereoselective synthesis, Sulfone alkylation, Wittig reaction",

author = "Li, {Shu Kun} and Rui Xu and Xiao, {Xiang Shu} and Bai, {Dong Lu}",

year = "2000",

doi = "10.1002/cjoc.20000180621",

language = "English (US)",

volume = "18",

pages = "910--923",

journal = "Chinese Journal of Chemistry",

issn = "1001-604X",

publisher = "Shanghai Institute of Organic Chemistry",

number = "6",

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TY - JOUR

T1 - A stereoselective synthesis of the C(3)-C(13) and C(14)-C(24) fragments of macrolactin A

AU - Li, Shu Kun

AU - Xu, Rui

AU - Xiao, Xiang Shu

AU - Bai, Dong Lu

PY - 2000

Y1 - 2000

N2 - Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.

AB - Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.

KW - Antiviral

KW - Julia olefination

KW - Macrolactin A

KW - Stereoselective synthesis

KW - Sulfone alkylation

KW - Wittig reaction

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U2 - 10.1002/cjoc.20000180621

DO - 10.1002/cjoc.20000180621

M3 - Article

AN - SCOPUS:0040487401

SN - 1001-604X

VL - 18

SP - 910

EP - 923

JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 6

ER -

A stereoselective synthesis of the C(3)-C(13) and C(14)-C(24) fragments of macrolactin A

Abstract

Keywords

ASJC Scopus subject areas

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