Synthetic Studies towards NG-121: Diastereoselective Synthesis of NG-121 Methyl Ether

Mandeep Singh; Narshinha P. Argade

doi:10.1055/s-0032-1317544

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(24): 3797-3804
DOI: 10.1055/s-0032-1317544

paper

Synthetic Studies towards NG-121: Diastereoselective Synthesis of NG-121 Methyl Ether

Mandeep Singh

Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India Fax: +91(20)25902629 eMail: np.argade@ncl.res.in

,

Narshinha P. Argade*

Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India Fax: +91(20)25902629 eMail: np.argade@ncl.res.in

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Abstract

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Abstract

Starting from unsymmetrically O-protected methyl 4-bromo-3,5-dihydroxybenzoate, a facile synthesis of the methyl ether of bioactive natural product NG-121 was accomplished in very good overall yield. The key steps were: Stille coupling reaction of the farnesyl unit with the electron-rich phenolic segment; hydroxy-directed selective epoxidation of the farnesyl chain along with concomitant phenol-driven intramolecular regio- and diastereoselective ring closure to the corresponding hydroxybenzopyran; and regioselective formylation followed by in situ reductive lactonization.

Key words

4-bromo-3,5-dihydroxybenzoate - Stille coupling - intramolecular cyclization - formylation - lactonization - NG-121 methyl ether

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Referenzen

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