SYNTHESIS OF HYDROXYMETHYL LACTONES AND SPIROKETALS VIA CYCLIZATION OF EPOXY OXACARBENE COMPLEXES

被引：5

作者：

MARSON, CM

RANDALL, L

WINTER, MJ

机构：

[1] Department of Chemistry, The University, Sheffield

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)73476-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metal acyls containing a terminal epoxide unit undergo cyclization with SnCl4 to give oxacarbene complexes that can be cleaved to hydroxymethyl lactones using pyridine N-oxide.

引用

页码：6717 / 6720

页数：4

共 23 条

[1] REACTIONS OF THE METALLABROMOALKANE [MO((CH2)3BR)(CO)3(ETA-C5H5)] AND THE CARBENE COMPLEXES TRANS-[MOI(=C(CH2)3O)(CO)2(ETA-C5H4R)](R=H OR ME) WITH LI(BET3H) - THE SYNTHESIS (R=H OR ME) AND X-RAY STRUCTURE (R=ME) OF [MO(CH(CH2)3O)(CO)2(ETA-C5H4R)] CONTAINING AN UNUSUAL OXYGEN MOLYBDENUM DONOR INTERACTIONH [J].

ADAMS, H ;

BAILEY, NA ;

CAHILL, P ;

ROGERS, D ;

WINTER, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1986, (10) :2119-2126

[2] CYCLIC CARBENE COMPLEXES OF MOLYBDENUM AND TUNGSTEN - CRYSTAL AND MOLECULAR-STRUCTURE OF [MOL(CO)2(CO(CH2)2CH2)(ETA-C5H5)] [J].

BAILEY, NA ;

CHELL, PL ;

MANUEL, CP ;

MUKHOPADHYAY, A ;

ROGERS, D ;

TABBRON, HE ;

WINTER, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1983, (11) :2397-2403

[3] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[4] METHYL AND ACETYL COMPLEXES OF CHROMIUM AND TUNGSTEN - OBSERVATIONS ON METAL-CARBON BOND STRENGTH VARIATIONS IN CHROMIUM TRIAD [J].

BARNETT, KW ;

BEACH, DL ;

GAYDOS, SP ;

POLLMANN, TG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 69 (01) :121-130

[5] COMPLEXES OF CYCLIC 2-OXACARBENES .1. SPONTANEOUS CYCLIZATION TO FORM COMPLEX OF 2-OXACYCLOPENTYLIDENE [J].

COTTON, FA ;

LUKEHART, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (11) :2672-+

[6] CARBONYL INSERTION REACTIONS OF METHYL- AND ETHYL-TRICARBONYLCYCLOPENTADIENYLMOLYBDENUM [J].

CRAIG, PJ ;

GREEN, M .

JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (08) :1978-&

[7] RELATIVE STEREOCHEMISTRY OF MULTISTRIATIN (2,4-DIMETHYL-5-ETHYL-6,8-DIOXABICYCLO[3.2.1]OCTANE) [J].

GORE, WE ;

PEARCE, GT ;

SILVERSTEIN, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (12) :1705-1708

[8] ANTIBODY CATALYSIS OF A DISFAVORED CHEMICAL TRANSFORMATION [J].

JANDA, KD ;

SHEVLIN, CG ;

LERNER, RA .

SCIENCE, 1993, 259 (5094) :490-493

[9] BARK BEETLE ATTRACTANTS - IDENTIFICATION SYNTHESIS AND FIELD BIOASSAY OF A NEW COMPOUND ISOLATED FROM DENDROCTONUS [J].

KINZER, GW ;

FENTIMAN, AF ;

PAGE, TF ;

FOLTZ, RL ;

VITE, JP ;

PITMAN, GB .

NATURE, 1969, 221 (5179) :477-&

[10] ENANTIOSPECIFIC SYNTHESIS OF 5-HEXADECANOLIDE, A PHEROMONE OF VESPA-ORIENTALIS [J].

LARCHEVEQUE, M ;

LALANDE, J .

TETRAHEDRON, 1984, 40 (06) :1061-1065

← 1 2 3 →