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A Short Synthesis of (R,R)-(-)-Pyrenophorin from (S)-Propylene Oxide and a 3-Pentenoic Acid d5-Reagent

✍ Scribed by Mali, Raghao S. ;Pohmakotr, Manat ;Weidmann, Beat ;Seebach, Dieter

Publisher: John Wiley and Sons
Year: 1981
Tongue: English
Weight: 751 KB
Volume: 1981
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198119811215

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✦ Synopsis

Abstract

Analysis of the known syntheses of pyrenophorin (1) (Scheme 1) reveals that they all rest upon the use of reagents with d^1^‐, d^3^‐, or a^2^‐reactivity umpolung for the establishment of at least one of the 1,4‐distances of functional groups. A different approach, outlined in Scheme 2, has now been realized: the non‐conjugated and the conjugated 7‐hydroxyoctenoic acids 10 and 11, obtained from dienone dianion derivatives of type 3 and d,l‐ or (S)‐methyloxirane, are converted to the macrodiolides 12 and 13, respectively. These are directly oxidized with introduction of an oxygen function at position 4, see 13 → 1 and 12 → 16 → 17 → 1. The overall transformation of the γ,δ‐unsaturated ketone 18 to pyrenophorin (1) in 27% yield takes six steps, partly without purification of intermediates.

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