Stereoselective Synthesis of the C₁₁-N₂₆ Fragment of Griseoviridin

Abstract

The C₁₁-N₂₆ fragment of griseoviridin has been prepared enantioselectively. The 1,3-syn diol synthon was derived from lipase-catalyzed selective acylation of (±)-1-(benzyloxy)pent-4-en-2-ol. The conjugated (E,E)-dienylmethyl azide functionality was installed by a Pd-catalyzed allylic azidation reaction.

Key words

alkenes - azides - antibiotics - catalysis - palladium

References

• 1 Ehrlich J. Coffey GL. Fisher MW. Galbraith MM. Knudsen MP. Sarber RW. Schlingman AS. Smith RM. Weston JK. Antibiot. Annu.  1955,  790 
• 2 Vazquez D. Antibiotics   Vol. III:  Corcoran JW. Hahn FE. Springer Verlag; New York: 1975. 
• 3 Birubaum GI. Hall SR. J. Am. Chem. Soc.  1976,  98:  1926 
• 4 Dvorak CA. Schmitz WD. Poon DJ. Pryde DC. Lawson JP. Amos RA. Meyers AI. Angew. Chem., Int. Ed.  2000,  39:  1664 
• 5a Meyers AI. Amos RA. J. Am. Chem. Soc.  1980,  102:  870 
• 5b Butera J. Rini J. Helquist P. J. Org. Chem.  1985,  50:  3676 
• 5c Liu L. Tanke RS. Miller MJ. J. Org. Chem.  1986,  51:  5332 
• 5d Marcantoni E. Massaccesi M. Petrini M. J. Org. Chem.  2000,  65:  4553 
• 6 Ghosh AK. Lei H. J. Org. Chem.  2000,  65:  4779 
• 7 Murahashi S. Taniguchi Y. Imada Y. Tanigawa Y. J. Org. Chem.  1989,  54:  3292 
• 8a Cocito C. Microbiol. Rev.  1979,  43:  145 
• 8b Service RF. Science  1995,  270:  724 
• 9 Burgess EM. Penton HR. Taylor EA. Williams WM. Org. Synth. Coll. Vol. VI   Wiley; New York: 1988.  p.788 
• 10 Williams DR. Lowder PD. Gu YG. Brooks DA. Tetrahedron Lett.  1997,  38:  331