Some transformations of cis-tetrahydrobenzopyran-2-ones: The precursor lactones to the trichothecenes

Authors
Ray, UK Ahmad, Z Venkateswaran, RV
Citation
Uk. Ray et al., Some transformations of cis-tetrahydrobenzopyran-2-ones: The precursor lactones to the trichothecenes, J INDIAN CH, 75(10-12), 1998, pp. 705-708
Citations number
16
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF THE INDIAN CHEMICAL SOCIETY
ISSN journal
00194522 → ACNP
Volume
75
Issue
10-12
Year of publication
1998
Pages
705 - 708
Database
ISI
SICI code
0019-4522(199810/12)75:10-12<705:STOCTP>2.0.ZU;2-K
Abstract
Attempted photolytic ethylene addition to lactone 3 affords only the intram olecular cycloadduct 5 and the rearranged product 6, the latter arising fro m a photo-ene reaction. Similarly lactone 4 also furnishes the cycloadduct 8 and the ene product 9. Basic hydrolysis of 6 followed by esterification p roduces the hydroxydiester 10 which on oxidation furnishes the highly funct ionalised bieyclo(3.2.1)octane derivative 11.