Total synthesis of the novel antifungal agent (±)-jesterone

被引：37

作者：

Mehta, G ^{[1
]}

Pan, SC ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol0499699

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the novel, biologically active epoxyquinone natural product (+/-)-jesterone has been accomplished from the readily accessible Diels-Alder adduct of cyclopentadiene and prenylated-p-benzoquinone. The approach delineated here is notable for its conceptual simplicity and efficient orchestration of a series of chemo-, regio-, and stereoselective operations.

引用

页码：811 / 813

页数：3

共 7 条

[1] BOUZBOUZ S, 1994, SYNTHESIS-STUTTGART, P714
[2] Exploring chemical diversity of epoxyquinoid natural products: Synthesis and biological activity of (-)-jesterone and related molecules
Hu, YB
Li, CM
Kulkarni, BA
Strobel, G
Lobkovsky, E
Torczynski, RM
Porco, JA
[J]. ORGANIC LETTERS, 2001, 3 (11) : 1649 - 1652
[3] LEY SV, 1994, SYNTHESIS-STUTTGART, P639
[4] Jesterone and hydroxy-jesterone antioomycete cyclohexenone epoxides from the endophytic fungus Pestalotiopsis jesteri
Li, JY
Strobel, GA
[J]. PHYTOCHEMISTRY, 2001, 57 (02) : 261 - 265
[5] Jesterone dimer, a synthetic derivative of the fungal metabolite jesterone, blocks activation of transcription factor nuclear factor κB by inhibiting the inhibitor of κB kinase
Liang, MC
Bardhan, S
Li, CM
Pace, EA
Porco, JA
Gilmore, TD
[J]. MOLECULAR PHARMACOLOGY, 2003, 64 (01) : 123 - 131
[6] Total synthesis of the novel angiogenesis inhibitors epoxyquinols A and B
Mehta, G
Islam, K
[J]. TETRAHEDRON LETTERS, 2003, 44 (17) : 3569 - 3572
[7] OXIDATION OF ALCOHOLS TO ALDEHYDES WITH OXYGEN AND CUPRIC ION, MEDIATED BY NITROSONIUM ION
SEMMELHACK, MF
SCHMID, CR
CORTES, DA
CHOU, CS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) : 3374 - 3376

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