Phorboxazole synthetic studies. 2. Construction of a C(20-28) subtarget, afurther extension of the Petasis-Ferrier rearrangement

Authors
Smith, AB Minbiole, KP Verhoest, PR Beauchamp, TJ
Citation
Ab. Smith et al., Phorboxazole synthetic studies. 2. Construction of a C(20-28) subtarget, afurther extension of the Petasis-Ferrier rearrangement, ORG LETT, 1(6), 1999, pp. 913-916
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
6
Year of publication
1999
Pages
913 - 916
Database
ISI
SICI code
1523-7060(19990923)1:6<913:PSS2CO>2.0.ZU;2-I
Abstract
[GRAPHICS] In this, the second of two Letters, we describe the efficient assembly of ( +)-4, a C(20-28) subtarget for the total synthesis of phorboxazoles A (1) a nd B (2), The synthesis was achieved in 12 linear steps (20% overall yield) via Petasis-Ferrier rearrangement of an NZ mixture of trisubstituted enol ethers (15) to assemble the C(22-26) cis-tetrahydropyran. A mechanism for t he observed diastereoconvergence of 15 is proposed, In addition, a new tact ic for the synthesis of enol ethers (e.g,, 15) based on the elegant work of Julia is described.