Asymmetric synthesis of palitantin from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone

被引：20

作者：

Hareau, G ^{[1
]}

Koiwa, M ^{[1
]}

Hanazawa, T ^{[1
]}

Sato, F ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 42期

基金：

日本学术振兴会;

关键词：

asymmetric synthesis; copper; copper compounds; cyclohexenones; hydroxylation;

D O I：

10.1016/S0040-4039(99)01549-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Palitantin (2) has been synthesized in 25% overall yield from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone [(R)-1] where a remarkable diastereoselective cat. OsO4 cis-dihydroxylation of (R)-1 furnished the precursor of the optically pure (5R,6R)-bis-trimethylsiloxy 2-cyclohexenone (7) which underwent highly selectively the 1,4-addition reaction of the 1,3-heptadienyl cyanocuprate to give, after trapping of the corresponding copper enolate with formaldehyde, the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7493 / 7496

页数：4

共 16 条

[1] STUDIES IN THE BIOCHEMISTRY OF MICRO-ORGANISMS .88. PALITANTIN .2. FURTHER DERIVATIVES AND DEGRADATION PRODUCTS [J].

BIRKINSHAW, JH .

BIOCHEMICAL JOURNAL, 1952, 51 (02) :271-276

[2] Studies in the biochemistry of micro-organisms. XLIX. Palitantin, C14H22O4, a hitherto undescribed metabolic product of Penicillium palitans Westling. [J].

Birkinshaw, JH ;

Raistrick, H .

BIOCHEMICAL JOURNAL, 1936, 30 :801-808

[3] THE STRUCTURE OF PALITANTIN [J].

BOWDEN, K ;

LYTHGOE, B ;

MARSDEN, DJS .

JOURNAL OF THE CHEMICAL SOCIETY, 1959, (MAY) :1662-1669

[4] HIGHLY SELECTIVE, KINETICALLY CONTROLLED ENOLATE FORMATION USING LITHIUM DIALKYLAMIDES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE [J].

COREY, EJ ;

GROSS, AW .

TETRAHEDRON LETTERS, 1984, 25 (05) :495-498

[5] FREQUENTIN - AN ANTIBIOTIC PRODUCED BY SOME STRAINS OF PENICILLIUM-FREQUENTANS WESTLING [J].

CURTIS, PJ ;

HEMMING, HG ;

SMITH, WK .

NATURE, 1951, 167 (4249) :557-558

[6]

DERUYTTERE X, 1992, SYNLETT, P51

[7] SYNTHESIS OF (+)-PALITANTIN [J].

HANESSIAN, S ;

SAKITO, Y ;

DHANOA, D ;

BAPTISTELLA, L .

TETRAHEDRON, 1989, 45 (21) :6623-6630

[8] Synthesis of optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone and its 6-substituted derivatives as useful chiral building blocks for the synthesis of cyclohexane rings.: Syntheses of carvone, penienone, and penihydrone [J].

Hareau, GPJ ;

Koiwa, M ;

Hikichi, S ;

Sato, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3640-3650

[9]

Hareau-Vittini G, 1998, ANGEW CHEM INT EDIT, V37, P2099, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2099::AID-ANIE2099>3.0.CO

[10]

2-U

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