Synthetic Applications of Asymmetric Horner-Wadsworth-Emmons Condensations: Approaches to Marine Natural Products

Abstract

Asymmetric HWE condensations of meso-dialdehyde 1 with chiral phosphonates containing 8-phenylmenthol very directly generate chiral moieties that are seen in a number of cytotoxic natural products. The HWE reactions proceed in good yields with synthetically useful geometric and diastereoselectivities. Also, we demonstrate the applicability of the HWE products to the synthesis of biologically active marine natural products.

Keywords::

• asymmetric Horner-Wadsworth-Emmons condensation
• chiral phosphonate
• desymmetrization
• doliculide
• meso-dialdehyde