Enantioselective synthesis of γ,δ-disubstituted β-hydroxy δ-lactones from furans:: Synthesis of (+)-prelactone B and its C-4 epimer

被引：33

作者：

Csáky, AG ^{[1
]}

Mba, M ^{[1
]}

Plumet, J ^{[1
]}

机构：

[1] Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

来源：

SYNLETT | 2003年 / 13期

关键词：

furans; cyclopentenones; lactones; natural products; stereoselective synthesis;

D O I：

10.1055/s-2003-42057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the enantioselective synthesis of gamma,delta-disubstituted beta-hydroxy delta-lactones (5,6-dialkyl-5,6-dihydropyran-2-ones) is reported and exemplified for (+)-prelactone B and its C-4 epimer. Our approach is based on the ring-enlargement of suitably functionalized optically pure 4-hydroxycyclopentanones, which are readily obtained from chiral 4-hydroxycyclopent-2-enones derived from furans. The procedure is amenable to the large-scale synthesis of the title compounds.

引用

页码：2092 / 2094

页数：3

共 18 条

[1] LIPASE-CATALYZED IRREVERSIBLE TRANSESTERIFICATION USING ENOL ESTERS - RESOLUTION OF PROSTAGLANDIN SYNTHONS 4-HYDROXY-2-ALKYL-2-CYCLOPENTENONES AND INVERSION OF THE 4S ENANTIOMER TO THE 4R ENANTIOMER [J].

BABIAK, KA ;

NG, JS ;

DYGOS, JH ;

WEYKER, CL ;

WANG, YF ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3377-3381

[2] METABOLIC PRODUCTS OF MICROORGANISMS .265. PRELACTONE-C AND PRELACTONE-B, OLIGOKETIDES FROM STREPTOMYCES PRODUCING CONCANAMYCINS AND BAFILOMYCINS [J].

BINDSEIL, KU ;

ZEECK, A .

HELVETICA CHIMICA ACTA, 1993, 76 (01) :150-157

[3]

CHARKRABORTY TK, 2003, TETRAHEDRON LETT, V44, P2541

[4] SYNTHESIS OF THERAPEUTICALLY USEFUL PROSTAGLANDIN AND PROSTACYCLIN ANALOGS [J].

COLLINS, PW ;

DJURIC, SW .

CHEMICAL REVIEWS, 1993, 93 (04) :1533-1564

[5] Regio- and stereoselective addition of Grignard and organolithium reagents to 4-hydroxy-2-cyclopentenones [J].

Csáky, AG ;

Mba, M ;

Plumet, J .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9026-9029

[6]

Fournier L, 2003, SYNLETT, P107

[7] The retro-Nazarov reaction [J].

Harmata, M ;

Lee, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14328-14329

[8] CYCLOPENTENONE DERIVATIVES .6. 4-OXO-2-CYCLOPENTENYL ACETATE - A SYNTHETIC INTERMEDIATE [J].

HARRE, M ;

RADDATZ, P ;

WALENTA, R ;

WINTERFELDT, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (07) :480-492

[9]

HEFELD O, 1999, SYNLETT, P401

[10] CHEMOENZYMATIC SYNTHESIS OF 1,3-DIDEOXYNOJIRIMYCIN [J].

JOHNSON, CR ;

GOLEBIOWSKI, A ;

BRAUN, MP ;

SUNDRAM, H .

TETRAHEDRON LETTERS, 1994, 35 (12) :1833-1834

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