SYNTHESIS OF NEOLIGNANS VIA A PROPOSED BIOSYNTHETIC INTERMEDIATE - TOTAL SYNTHESIS OF (+ -)-FUTOENONE/

Citation
Sr. Angle et Kd. Turnbull, SYNTHESIS OF NEOLIGNANS VIA A PROPOSED BIOSYNTHETIC INTERMEDIATE - TOTAL SYNTHESIS OF (+ -)-FUTOENONE/, Journal of organic chemistry, 58(20), 1993, pp. 5360-5369
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
58
Issue
20
Year of publication
1993
Pages
5360 - 5369
Database
ISI
SICI code
0022-3263(1993)58:20<5360:SONVAP>2.0.ZU;2-M
Abstract
The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. T he results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo[3.2.1]octenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (+/-)-futoenone via a benzylic cation intermediate related to quinone methide 3 is reported. The res ults provide support for Gottlieb's proposal that several different ne olignans arise from a common biosynthetic precursor. The efficient syn thesis of (+/-)-futoenone and related spiro[5.5]undecanoids using a Bu chi quinone ketal cycloaddition is also described.