Biosynthesis of the Ephedra Alkaloids - mdma.ch

Biosynthesis of the Ephedra Alkaloids - mdma.chpubs.acs.org/doi/pdf/10.1021/ja00058a070?src=recsysgraphite monochromator (X(KaJ = 0.709 30 A); 4O 5 20...
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J . Am. Chem. SOC.1993, 115, 2052-2054

2052

to establish which other dienes display the same dimerization behavior as 1,3-COD and to determine which functional groups may be tolerated during such metal-mediated coupling processes.

Scheme I

Acknowledgment. We are grateful to the Natural Sciences and Engineering Research Council of Canada for support of this work in the form of grants to P.L. and F.W.B.E. and a postgraduate scholarship to J.D.D. Supplementary Material Available: Experimental procedures and characterization data for all complexes and full details of the crystal structure analyses including associated tables for C P * M O ( N O ) ( C ~ ~ (14 H ~ pages); ~) tables of measured and calculated structure factor amplitudes for C P * M O ( N O ) ( C ~ ~ (18 H~~) pages). Ordering information is given on any current masthead page.

Biosynthesis of the Ephedra Alkaloids: Evolution of the C d 3 Skeleton sn

actions depicted in Scheme I do not permit an unambiguous assignment of their molecular structures. Consequently, we have subjected C ~ * M O ( N O ) ( C ~to ~H a single-crystal ~~) X-ray crystallographic analysis.' The carbon-carbon bond lengths within the C16H24ligand of C ~ * M O ( N O ) ( C ~ ~indicate H ~ ~ ) the existence of three C=C linkages as shown in Scheme I, namely, C(2)-C(3) [1.392(3) A] and C(12)-C(13) [1.383(3) A ] , each of which is involved in T~ r-bonding to Mo with an average Mo-C = 2.34 A, and C(1 I)25,0.15,and10%,respectively. Atrace(