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

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[26] SYNTHESIS OF ENANTIOMERICALLY PURE (5S)-4-AZA-2-OXA-6,6-DIMETHYL-7,10-METHYLENE-5-SPIRO[4.5] DECAN-3-ONE, A NOVEL CHIRAL OXAZOLIDIN-2-ONE FROM (-)-CAMPHENE FOR USE AS A RECYCLABLE CHIRAL AUXILIARY IN ASYMMETRIC TRANSFORMATIONS
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