Download Fortschritte der Chemie Organischer Naturstoffe / Progress by Prof. Dr. O. R. Gottlieb, Prof. Dr. rer. nat. K. Herrmann, PDF

By Prof. Dr. O. R. Gottlieb, Prof. Dr. rer. nat. K. Herrmann, Dr. R. D. H. Murray, Dr. G. Ohloff, Prof. Dr. G. Pattenden (auth.), W. Herz, H. Grisebach, G. W. Kirby (eds.)

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M) ... I. Br2, CaC0 3, CHCI 3; 2. KOH, refl. Chart 23. 1a) 0 O. R. 56 GOTTLIEB: as well as the ring opened products 82a, b, c, d, e. Since it was possible to reconvert these into futoenone, they not only supported the spirodienone structure for the compound, but were also useful in the accomplishment of the total synthesis which employed the Knoevenagel adduct 84 as key intermediate (Chart 23) (115). Assignment of the relative stereochemistry 85 to futoenone was based on interpretation of the coupling constants of the cyclohexane protons and the appearance of the secondary methyl signal at high field, indicating its orientation with respect to the dienone ring.

Ac 2 0. (D) ... HCI, MeOH. Chart 21. 10a) References, pp. 65-72 Neolignans 45 VII. 1' -Neolignans 1. 1a was accorded by consideration of IR, UV and 220 MHz lH NMR spectral data (21). The MS was of little help in the analysis. The rearrangements which seem to account for some of the major peaks could only be formulated with confidence a posteriori (Chart 22). ;h t\ \ '<::::: Pi/""-O ~ t M-30 OMe ~O 1+· ~(--- 0 . 0 Pi o :ccc Pi l+· o l+· ~ Pi. 1a) l+. t ) l+· I __--+-_ Pi I + ~OMe Pi~O~/):O Chart 22.

LiAI~, Et,O; 2. H2 , 100/0 PdIC, AcOEt. Chart 11. Synthesis of dehydro-otobaphenol ethyl ether (36) References, pp. 65-72 Neolignans 33 (A) -----+ MeO MeO EtO EtO OMe OMe OMe OEt t(C) ~ OEt (B) o MeO~OEt EtO~OMe o (A) ... K 2 Cr 2 0" AcOH, 100°. (B) ... Cr03, AcOH - H 2 0, refl. (C) ... , refl. Chart 12. 1b). This, isolated in later years, had its structure confirmed by synthesis of the dehydrogenation product of the derived ethyl ether 36 (Chart 11) (88). 5a) were equally isolated only as ethers after methylation or ethylation of a phenolic resin.

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