TANDEM PERICYCLIC-REACTIONS - THE 1ST X-RAY STRUCTURE OF AN INITIAL PYRONE-OLEFIN ADDUCT AND AN EASY, STEREOCONTROLLED, ENTRY INTO POLYOXYGENATED CYCLOHEXANES

被引：36

作者：

MARKO, IE

SERES, P

SWARBRICK, TM

STATON, I

ADAMS, H

机构：

[1] Department of Chemistry, The University, Sheffield

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)61170-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under high-pressure conditions, 2-pyrone undergoes Diels-Alder reaction with a variety of dienophiles, leading to isolable, bridged, bicyclic lactones. The first X-Ray structure of one of these lactones and its conversion into polyoxygenated cyclohexane derivatives is reported.

引用

页码：5649 / 5652

页数：4

共 14 条

[1] TOTAL SYNTHESIS OF MYCOPHENOLIC-ACID
DANHEISER, RL
GEE, SK
PEREZ, JJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) : 806 - 810
[2] HIGH-PRESSURE CYCLOADDITIONS OF PYRONES - SYNTHESIS OF HIGHLY FUNCTIONALIZED 6-MEMBERED RINGS BY INHIBITION OF CARBON-DIOXIDE LOSS
GLADYSZ, JA
LEE, SJ
TOMASELLO, JAV
YU, YS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (25) : 4170 - 4172
[3] HARANO K, 1990, CHEM PHARM BULL, V38, P1182
[4] ASPECTS OF STEREOCHEMISTRY .1. STEREOSPECIFICITY IN FORMATION OF EPOXIDES FROM CYCLIC ALLYLIC ALCOHOLS
HENBEST, HB
WILSON, RAL
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAY): : 1958 - 1965
[5] CONJUGATED KETENES - NEW ASPECTS OF THEIR SYNTHESIS AND SELECTED UTILITY FOR THE SYNTHESIS OF PHENOLS, HYDROQUINONES, AND QUINONES
MOORE, HW
DECKER, OHW
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 821 - 830
[6] [2,3]-WITTIG SIGMATROPIC REARRANGEMENTS IN ORGANIC-SYNTHESIS
NAKAI, T
MIKAMI, K
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 885 - 902
[7] SYNTHESIS OF SOME 3-OXO-2-OXABICYCLO[2.2.2]OCT-7-ENE DERIVATIVES AND ATTEMPTS OF THEIR CONVERSION INTO 3-OXO-2-OXABICYCLO[2.2.2]OCTA-5,7-DIENE
PFAFF, E
PLIENINGER, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1982, 115 (05): : 1967 - 1981
[8] STEREOCONTROLLED SYNTHESIS OF A TRIHYDROXYLATED A RING AS AN IMMEDIATE PRECURSOR TO 1-ALPHA,2-ALPHA,25-TRIHYDROXYVITAMIN-D3
POSNER, GH
NELSON, TD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) : 4339 - 4341
[9] 3-BROMO-2-PYRONE - AN EASILY PREPARED CHAMELEON DIENE AND A SYNTHETIC EQUIVALENT OF 2-PYRONE IN THERMAL DIELS-ALDER CYCLOADDITIONS
POSNER, GH
NELSON, TD
KINTER, CM
AFARINKIA, K
[J]. TETRAHEDRON LETTERS, 1991, 32 (39) : 5295 - 5298
[10] Sharpless K. B., 1979, ALDRICHIM ACTA, V12, P63

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