Tetrahedron Letters

Synthetic studies toward the microtubule-stabilizing agent laulimalide: synthesis of the C 1–C 14 fragment

GT Nadolski, BS Davidson

Index: Nadolski, Geoffry T.; Davidson, Bradley S. Tetrahedron Letters, 2001 , vol. 42, # 5 p. 797 - 800

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Citation Number: 39

Abstract

The C1–C14 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 15 steps from l-(−)-citronellal. The C9 chiral center was established using an asymmetric allylation, the dihydropyran ring was prepared through ring-closing metathesis, and the exo-methylene was incorporated using Eschenmoser's salt.