Phorboxazole Synthetic Studies. 2. Construction of a C(20−28) Subtarget, a Further Extension of the Petasis−Ferrier Rearrangement
Autor: | Kevin P. C. Minbiole, Amos B. Smith, Thomas J. Beauchamp, Patrick R. Verhoest |
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Rok vydání: | 1999 |
Předmět: | |
Zdroj: | Organic Letters. 1:913-916 |
ISSN: | 1523-7052 1523-7060 |
Popis: | [formula: see text] 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) and B (2). The synthesis was achieved in 12 linear steps (20% overall yield) via Petasis-Ferrier rearrangement of an E/Z mixture of trisubstituted enol ethers (15) to assemble the C(22-26) cis-tetrahydropyran. A mechanism for the observed diastereoconvergence of 15 is proposed. In addition, a new tactic for the synthesis of enol ethers (e.g., 15) based on the elegant work of Julia is described. |
Databáze: | OpenAIRE |
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