Brevicomin synthesis

BPE, and chiral bisphosphane ligands, 10, 7 (+)-Brasilenyne, via ring-closing diene metathesis, 11, 221 Breast implants, silicone applications, 3, 680 Brevetoxin B, via ring-closing diene metathesis, 11, 237 m -Brevicomin, synthesis, 9, 13... 

Kavirayani R. Prassad s elegant brevicomin synthesis starts also from tartaric add, although actually from its Weinreb amide, which is converted into the desired intermediate hy a double Grignard reaction. Other key steps in the synthesis are the lead tetraacetate-mediated cleavage of the diol and the Wacker oxidation of the terminal alkene. [204]... 

More genuine examples of intramolecular oxypalladation applied to the natural product synthesis involve conversion of alkenediols into cyclic acetals, as exemplified by the synthesis of brevicomint t and frontalint t shown in Scheme 4. The brevicomin synthesis reported in 1976 may well be the first reported example of the application of intramolecular oxypalladation to the synthesis of natural products. 

Reaction with Alcohols and Phenols. The reaction of alcohols with terminal alkenes affords acetals of ketones (eq 9). An elegant application of the reaction was a brevicomin synthesis (eq 10). ... 

---