A STEREOSELECTIVE SYNTHESIS OF MEDIUM-SIZED CYCLIC ETHERS BY THE INTRAMOLECULAR CYCLIZATION OF LINEAR HYDROXYALKYL-PROPARGYLIC ALCOHOLS ASSISTED BY CO-2(CO)(8)

被引：48

作者：

PALAZON, JM ^{[1
]}

MARTIN, VS ^{[1
]}

机构：

[1] UNIV LA LAGUNA, INST UNIV BIOORGAN, CTR PROD NAT ORGAN ANTONIO GONZALEZ, E-38206 LA LAGUNA, SPAIN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 20期

关键词：

D O I：

10.1016/0040-4039(95)00555-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient, mild and general cyclization reaction of hydroxy exo-(propargyl)Co-2(CO)(6) cations leading to medium-sized (6 to 9 membered) cyclic ethers is described. The reaction is highly stereoselective when defined stereocenters are encountered in the linear precursor, providing a way to obtain fused cyclic ethers in their enantiomeric forms.

引用

页码：3549 / 3552

页数：4

共 44 条

[1] SIMPLE DESIGNS FOR THE CONSTRUCTION OF COMPLEX TRANS-FUSED POLYETHER TOXIN FRAMEWORKS - A LINEAR STRATEGY BASED ON ENTROPICALLY FAVORED OXIRANE RING ENLARGEMENT IN EPOXYCYCLOALKENES FOLLOWED BY CARBON-CARBON OR CARBON-OXYGEN BOND-FORMING CYCLIZATIONS [J].

ALVAREZ, E ;

DIAZ, MT ;

PEREZ, R ;

RAVELO, JL ;

REGUEIRO, A ;

VERA, JA ;

ZURITA, D ;

MARTIN, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) :2848-2876

[2] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-ISOLAUREPINNACIN [J].

BERGER, D ;

OVERMAN, LE ;

RENHOWE, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9305-9306

[3] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[4] STEREOSELECTIVE PROPARGYLATION MEDIATED BY A CHIRAL METAL CLUSTER - REACTIONS OF [(PROPARGYLIUM)CO2(CO)5-(P(OR)3)][BF4] WITH CARBON NUCLEOPHILES [J].

CAFFYN, AJM ;

NICHOLAS, KM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6438-6439

[5]

Erickson K. L., 1979, MARINE NATURAL PRODU, V5, P131, DOI DOI 10.1016/B978-0-12-624005-4.50011-2

[6] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1991, 8 (02) :97-147

[7] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1990, 7 (04) :269-309

[8] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1988, 5 (06) :613-663

[9] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1987, 4 (05) :539-576

[10] MARINE NATURAL-PRODUCTS [J].

FAULKNER, DJ .

NATURAL PRODUCT REPORTS, 1986, 3 (01) :1-33

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