Total synthesis of the epidermal growth factor inhibitor (-)-reveromycin B

…, CA Hutton, MJ Lilly, RK Mann, KJ McRae…

Index: Cuzzupe; Hutton; Lilly; Mann; McRae; Zammit; Rizzacasa Journal of Organic Chemistry, 2001 , vol. 66, # 7 p. 2382 - 2393

Full Text: HTML

Citation Number: 68

Abstract

The total synthesis of the epidermal growth factor inhibitor reveromycin B (2) in 25 linear steps from chiral methylene pyran 13 is described. The key steps involved an inverse electron demand hetero-Diels-Alder reaction between dienophile 13 and diene 12 to construct the 6, 6-spiroketal 11 which upon oxidation with dimethyldioxirane and acid catalyzed rearrangement gave the 5, 6-spiroketal aldehyde 9. Lithium acetylide addition ...