250355-75-0Relevant academic research and scientific papers
Total synthesis of (+)-phorboxazole A exploiting the Petasis-Ferrier rearrangement
Smith III,Minbiole,Verhoest,Schelhaas
, p. 10942 - 10953 (2007/10/03)
A highly convergent, stereocontrolled total synthesis of the potent antiproliferative agent (+)-phorboxazole A (1) has been achieved. Highlights of the synthesis include: modified Petasis-Ferrier rearrangements for assembly of both the C(11 - 15) and C(22-26) cis-tetrahydropyran rings; extension of the Julia olefination to the synthesis of enol ethers; the design, synthesis, and application of a novel bifunctional oxazole linchpin; and Stille coupling of a C(28) trimethyl stannane with a C(29) oxazole triflate. The longest linear sequence leading to (+)-phorboxazole A (1) was 27 steps, with an overall yield of 3%.
Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement
Smith III, Amos B.,Verhoest, Patrick R.,Minbiole, Kevin P.,Lim, John J.
, p. 909 - 912 (2008/02/09)
(equation presented) In this, the first of two Letters, we outline our overall strategy for the total synthesis of phorboxazoles A (1) and B (2), rare oxazole-containing macrolides possessing extraordinary antimitotic activity, and describe the assembly o
