Synthetic studies on arene-olefin cycloadditions - V. total synthesis of (±)-isoiridomyrmecin.

✍ Scribed by Paul A Wender; Geoffrey B Dreyer

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 239 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85950-x

✦ Synopsis

An eight step synthesis of the iridoid isoiridomyrmecin is described, in which new methodology for the stereooontrolled elaboration of arene-olefin oycloadducts is delineated.

The arene-olefin cycloadditionlr* provides a general approach to polyquinane synthesis in which a tricyclo[3.3.0.02~*lcctene derivative is efficiently assembled in one step with the development of up to six stereocenters. Recently, we described the use of this process for the preparation of the indan -vinyl acetate oycloadduct 5, from which (s-modhepheneld

(1) was synthesized via the intermediates 4, 3, and 2. This design served to establish the basis for analogous direct routes to other classes of five-membered ring compounds including iridoid monoterpenes3 and the pharmacologically important oarbaprostacyclins. Ths extension of this methodology to the problem of iridoid synthesis is described herein in a total synthesis of the ant defensive secretion, isoiridomyrmecin (614.