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Novel reactions of a deltaline analog: an unusual skeletal rearrangement of E/F ring system
- Source :
- Tetrahedron. 68:5031-5036
- Publication Year :
- 2012
- Publisher :
- Elsevier BV, 2012.
-
Abstract
- Lactam 2, prepared from deltaline (1), is an analog of C19-diterpenoid alkaloid with a hydroxyl group at C-6 and a ketone carbonyl group at C-7. Treatment of this lactam with thionyl chloride or methanesulfonyl chloride, or reaction of this lactam under Chugaev condition led to an unusual rearrangement of its E/F ring system to yield a lactone 10 in a yield range of 43–74%. The structure of 10 was confirmed by its 2D NMR data and X-ray crystallographic analysis.
Details
- ISSN :
- 00404020
- Volume :
- 68
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........90295f08233acc2fd7a1dbaa6d4cc446