A carbanion induced ring switching synthesis of spiranes: an unprecedented approach

被引：9

作者：

Maurya, Hardesh K. ^{[1
,5
]}

Pratap, Ramendra ^{[3
]}

Kumar, Abhinav ^{[1
]}

Kumar, Brijesh ^{[2
]}

Huch, Volker ^{[4
]}

Tandon, Vishnu K. ^{[1
]}

Ram, Vishnu Ji ^{[1
]}

机构：

[1] Univ Lucknow, Dept Chem, Lucknow 226007, Uttar Pradesh, India

[2] Cent Drug Res Inst, Div SAIF, Lucknow 226001, Uttar Pradesh, India

[3] Univ Delhi, Dept Chem, Delhi 110007, India

[4] Univ Saarland, Inst Inorgan Chem, D-6600 Saarbrucken, Germany

[5] Cent Inst Med & Aromat Plants, Dept Med Chem, Lucknow 226015, Uttar Pradesh, India

来源：

RSC ADVANCES | 2012年 / 2卷 / 24期

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; CLOSING METATHESIS; FREDERICAMYCIN-A; CYCLO-ADDITIONS; MODEL; REARRANGEMENT; CYCLOADDITION; DERIVATIVES; CONVERSION; SEQUENCE;

D O I：

10.1039/c2ra21587j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unique approach to the synthesis of heterocyclic spiranes through ring switching transformation of suitably functionalized 2H-pyran-2-ones, benzo[h]chromene and thiochromeno[4,3-b]pyrans has been developed. The spirane dimer 11d displayed interesting halogen-hydrogen bonding to generate an elliptical cavity and may be relevant to the generation of a host guest assembly for specific cations and also a low helimerization energy barrier of spirane 17a.

引用

页码：9091 / 9099

页数：9

共 84 条

[1] Atta-ur-Rahman, 1989, STUDIES NATURAL PROD
[2] MODEL STUDIES AIMED AT THE SYNTHESIS OF FREDERICAMYCIN-A - A SIMPLE O-QUINODIMETHANE ROUTE TO THE SPIRO NAPHTHALENE PORTION
BACH, RD
KLIX, RC
[J]. TETRAHEDRON LETTERS, 1986, 27 (18) : 1983 - 1986
[3] CONCERTED 1,2-CARBONYL MIGRATIONS IN ORGANIC-SYNTHESIS - A PRACTICAL SYNTHESIS OF SPIRO CYCLIC 1,3-DIKETONES
BACH, RD
KLIX, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) : 5438 - 5440
[4] A concise total synthesis of (±)-bakkenolide A by means of an intramolecular Diels-Alder reaction
Back, TG
Payne, JE
[J]. ORGANIC LETTERS, 1999, 1 (04) : 663 - 665
[5] Barone V, 1998, J COMPUT CHEM, V19, P404, DOI 10.1002/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO
[6] 2-W
[7] Spirocycle assembly through selective tandem ring closing metathesis reactions
Bassindale, MJ
Hamley, P
Leitner, A
Harrity, JPA
[J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3247 - 3250
[8] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
BECKE, AD
[J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
[9] Bjornstad V., 2008, SYNTHESIS-STUTTGART, P962
[10] CALCULATION OF SMALL MOLECULAR INTERACTIONS BY DIFFERENCES OF SEPARATE TOTAL ENERGIES - SOME PROCEDURES WITH REDUCED ERRORS
BOYS, SF
BERNARDI, F
[J]. MOLECULAR PHYSICS, 1970, 19 (04) : 553 - &

← 1 2 3 4 5 6 7 8 9 →