Total Synthesis of (+)-Phorboxazole A Exploiting the Petasis−Ferrier Rearrangement
- 13 October 2001
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 123 (44) , 10942-10953
- https://doi.org/10.1021/ja011604l
Abstract
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%.Keywords
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