Catalytic oxidation of pentacyclo[6.6.0(2,6).0(3,13).0(10,14)]tetradeca-4,11-diene. Syntheses of novel polyfunctional half-open cage compounds

Authors
Suzuki, T Iida, K Wada, K Kondo, T Mitsudo, TA
Citation
T. Suzuki et al., Catalytic oxidation of pentacyclo[6.6.0(2,6).0(3,13).0(10,14)]tetradeca-4,11-diene. Syntheses of novel polyfunctional half-open cage compounds, TETRAHEDR L, 40(15), 1999, pp. 2997-3000
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
15
Year of publication
1999
Pages
2997 - 3000
Database
ISI
SICI code
0040-4039(19990409)40:15<2997:COOP>2.0.ZU;2-#
Abstract
Oxidation of pentacyclo[6.6.0.0(2.6).0(3,13).0(10.14)]tetra l-diene, PCTD, with hydrogen peroxide catalyzed by methyltrioxorhenium selectively gave th e exo,exo-diepoxide in high yield. Osmium tetraoxide catalyzed selective sy n-exo-tetrahydroxylation or syn-exo-dihydroxylation of PCTD with N-methylmo rphorine N-oxide. Ruthenium trichloride-catalyzed oxidative cleavage of the olefinic groups in PCTD with sodium periodate gave a derivative of tricycl odecanecarboxylic acid with two lactone rings. (C) 1999 Elsevier Science Lt d. All rights reserved.