Heterocycles p. 291 - 298 (2006)
Update date:2022-08-29
Topics:
Moldvai, Istvan
Temesvari-Major, Eszter
Gacs-Baitz, Eszter
Incze, Maria
Doernyei, Gabor
Szantay, Csaba
The double bond in ring D of (+)-9,10-didehydro-6-methylergolin-8-one (2) was reduced selectively by catalytic hydrogenation to yield (-)-6-methylergolin-8-one (6). Grignard reaction of 6 has been performed with methylmagnesium iodide to afford two isomers (5 and 7). The main isomer having an 8α-methyl group at C8 with a C/D-trans junction (5; (-)-dihydroisosetoclavine) proved to be identical with the natural product, hence its name and structure should be corrected. As a minor isomer (7) a C/D-cis clavine derivative was also isolated which can be regarded as unnatural (+)-8α-hydroxycostaclavine. (+)-Setoclavine (8) and (+)-isosetoclavine (9) have also been prepared from 2, thus achieving the first total synthesis of these natural products. Detailed structure elecidation of 5-9 has been carried out as well.
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