ChemInform Abstract: Alkenyl Diols by E-Selective Horner—Wittig Elimination: Formal Synthesis of any Isomer (RR, RS, SR or SS) Bearing 1,5-Related Stereogenic Centers Across an E Double Bond.

✍ Scribed by A. NELSON; S. WARREN

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199822062

✦ Synopsis

Alkenyl Diols by E-Selective Horner-Wittig Elimination: Formal Synthesis of any Isomer (RR, RS, SR or SS) Bearing 1,5-Related Stereogenic Centers Across an E Double Bond.

-A flexible strategy for the synthesis of (E)-alkenyl 1,5-diols [cf. (IV)] bearing related stereogenic centers is presented. Oxidative rearrangement of diastereomerically pure diphenylphosphinoyl furans (I) followed by NaBH 4 reduction gives triols (III) with four stereochemically controlled centers. (E)-selective Horner-Wittig elimination leads to diols (IV) with 1,5-related stereogenic centers across a trans double bond. -(NELSON, A.;