Thc reactions leading to the establishment of structure I for lycopodine are discussed. S t r u c t~~r e s are proposed for three cyclizatioll products derived from lycopodine.I n a short comlnunication (1) we proposed structure I for lycopodine. This structure has been confirmed by the worlt of Anet (2), who succeeded in interconverting several Lycopodiz~m alkaloids, among which was lycopodine. In this paper we wish to give a full account of our worlt on the elucidation of the structure of the alltaloid and t o discuss the structures of the tetracylic compounds obtained on elimination of hydrogen halide from lycopodine methiodide and a-and P-cyanobromolycopodine.
Structural revisions are made to products IT has recently been reported that reaction of natural formed when (-)-rotenone is treated with boron tri-(6aS,12aS,5'R)-(-)-rotenone (1) with 1 mol. equiv. of bromide; stereospecific labelling of the 4' ( E ) methyl of BBr, gives the 1',5'-seco-bromide (2), whilst with 2 mol. (-)-rotenonic acid, a biosynthetic precursor of rotenone, equiv. of BBr, gives (3).ls2 Treatment of (2) with HC0,can be achieved by treating product (4) with cyano-provides the only method available for making (5's)borodeuteride in hexamethylphosphorotamide.rotenone, which is formed along with the (5'R)-diastereoisomer. However, structures (2) and (3) appeared a t
Behandlung von (‐)‐Rotenon (Ia) mit l mol BBr3 liefert das Ring‐E‐Spaltungsprodukt (II), das weiter in die Verbindungen (IIIa) bzw. (IIIb) sowie (IIIc)‐(IIIe) übergeführt wird.
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