(+)-Cystothiazole G: isolation and structural elucidation

被引：19

作者：

Akita, H

Sasaki, T

Kato, K

Suzuki, Y

Kondo, K

Sakagami, Y

Ojika, M

Fudou, R

Yamanaka, S

机构：

[1] Toho Univ, Sch Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

[2] Nagoya Univ, Grad Sch Bioagr Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

[3] Ajinomoto Co Inc, Inst Life Sci, Kawasaki Ku, Kawasaki, Kanagawa 2108681, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 21期

关键词：

(+)-cystothiazole G; cyclization-methoxycarbonylation; chiral synthesis;

D O I：

10.1016/j.tet.2004.03.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpent-4-yne-1,2-diol (6) derived froth (2R,3S)epoxybutanoate 5 followed by methylation gave the tetrahydro-2-furylidene acetate (-)-7, which was converted to the left-half aldehyde (+)-3. A Wittig reaction between (+)-3 and the phosphoranylide derived froth the bithiazole-type phosphonium iodide 4 using lithium bis(trimethylsilyl)amide afforded the (+)-cystothiazole G (2), whose spectral data were identical with those of the natural product (+)-2. Thus, the stereochemistry of cystothiazole G (2) was proved to be (4R,5S,6(E)). (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4735 / 4738

页数：4

共 7 条

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