Synthesis and photoreactions of 3-oxa-tricyclo[5.2.2.01,5]undecenones:: a novel, stereoselective route to oxa-triquinanes and oxa-sterpuranes

被引：13

作者：

Singh, V ^{[1
]}

Alam, SQ ^{[1
]}

Praveena, GD ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

TETRAHEDRON | 2002年 / 58卷 / 48期

关键词：

Diels-Alder reaction; cycloaddition; photo-chemistry; oxapolyquinanes;

D O I：

10.1016/S0040-4020(02)01280-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 11-methyl-3-oxa-tricyclo[5.2.2.0(1,5)] undecenones and their photochemical reactions upon triplet (3 T) and singlet (S-1) excitation is described. Oxidation of hydroxymethylphenol gave a ketoepoxide by intramolecular cycloaddition. Manipulation of the oxirane ring furnished the chromophoric systems. Triplet excitation of these gave tetracyclic compounds containing an oxatriquinane framework. Singlet excitation furnished the tricyclic compound having an oxasterpurane ring system in a stereoselective fashion. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：9729 / 9736

页数：8

共 26 条

[1] Structural diversity through intramolecular cycloaddition and modulation of chemical reactivity in excited state.: Synthesis and photoreactions of 3-oxa-tricyclo[5.2.2.01,5]undecenones:: Novel stereoselective route to oxa-triqninanes and oxa-sterpuranes
Singh, V
Alam, SQ
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (22) : 2517 - 2519
[2] Molecular complexity from aromatics:: A novel, stereoselective route to tricyclo[5.2.2.01,5]undecenones, tricyclo[6.2.2.01,6]dodecenones, and [n.3.3]propellanes
Singh, Vishwakarma
Sahu, Pramod K.
Singh, Raj Bahadur
Mobint, Shaikh M.
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26): : 10155 - 10165
[3] Stereoselective synthesis of linear oxa-triquinanes and oxa-diquinanes via Lewis acid mediated nucleophilic addition to oxonium ions: study of nucleophile-dependent selectivity
Gharpure, Santosh J.
Niranjana, P.
Porwal, Suheel K.
ARKIVOC, 2022, : 220 - 238
[4] Base-assisted intramolecular 6-acetoxypyranone-acetylene [5+2] cycloaddition.: Synthesis and reactivity of novel oxa-tricyclo[5.3.1.01,5]undecenones
Celanire, S
Marlin, F
Baldwin, JE
Adlington, RM
TETRAHEDRON, 2005, 61 (12) : 3025 - 3032
[5] Oxidative dearomatization and unusual intramolecular Diels-Alder reaction of cyclohexa-2,4-dienone: synthesis and photoreaction of oxa-tricyclo[5.2.2.01,5]undec-10-ene-8-ones
Singh, Vishwakarma
Das, Beauty
TETRAHEDRON LETTERS, 2015, 56 (15) : 1982 - 1985
[6] Asymmetric Diels-Alder reaction of optically active 3-(3,3,3-trifluoropropenylsulfonyl)oxazolidine:: Synthesis of (8R)-8-trifluoromethyl-2-oxa-6-thia-5-azatricyclo[5.2.2.01,5]-undecane-6,6-dioxide
Okano, T
Nagai, T
Eguchi, S
Kimoto, H
HETEROCYCLES, 1999, 50 (01) : 53 - 56
[7] Stereoselective synthesis of pentacarbonyl(3-oxa-2-bicyclo[3.1.0]hexylidene)- and pentacarbonyl(cyclopropylmethoxymethylene)tungsten compounds on the route to cyclopropane-γ-lactones and -carboxylates
Florio, S
Perna, FM
Luisi, R
Barluenga, J
Fañanás, FJ
Rodríguez, F
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (26): : 9204 - 9207
[8] An improved synthesis of 2-oxa-7-azaspiro[3,5]nonane and analogs as novel reagents in medicinal chemistry
Xu, Ruo
Czarniecki, Michael
de Man, Jos
Pan, Jianping
Qiang, Li
Root, Yuriko
Ying, Shihong
Su, Jing
Sun, Xijun
Zhang, Yuping
Yu, Tao
Zhang, Yang
Hu, Tao
Chen, Shu-Hui
TETRAHEDRON LETTERS, 2011, 52 (26) : 3266 - 3270
[9] A Novel Ring-Enlargement Reaction of (3-Oxa-2-silacyclopentyl)methyl Radicals into 4-Oxa-3-silacyclohexyl Radicals. Stereoselective Introduction of a Hydroxyethyl Group via Unusual 6-Endo-Cyclization Products Derived from 3-Oxa-4-silahexenyl Radicals and Its Application to the Synthesis of a 4'-a-Branched Nucleoside
Shuto, S.
Kanazaki, M.
Ichikawa, S.
Matsuda, A.
Journal of Organic Chemistry, 62 (17):
[10] Synthesis of a novel series of 10-oxa-3-aza-tricyclo[5.2.1.01,5]dec-8-en-4-ones through an intramolecular Diels-Alder reaction
Milkiewicz, KL
Neagu, IB
Parks, DJ
Lu, TB
TETRAHEDRON LETTERS, 2003, 44 (39) : 7341 - 7343

← 1 2 3 →