Total synthesis of dehydroambliol-A and its unnatural Z isomer

Abstract

to our colleagues, Profs. D. Locke (Queens), G. Quigley, and M. Blumenstein (Hunter) for their invaluable technical assistance.Supplementary Material Available: X-ray crystallography material for urethane 15 (10 pages). Ordering information is given on any current masthead page.

A Divergent Synthesis of the Δ13-9-Isofurans

“…The nitrile group was hydrolyzed17 with 15% aqueous NaOH in EtOH at 85 °C, and the desired carboxylic acid 1aaa was isolated in excellent yield. Isofuran 1aab was prepared in the same way.…”

New Synthetic Methods for Hypericum Natural Products

“…The diketone 73 was synthesized based on Rothberg's protocol in his synthesis of dehydroambliol-A. 29 The synthesis began with condensation of 6-methyl-5-hepten-2-one and methyl benzoate to produce diketone 70 (Scheme 20 …”

Synthetic efforts toward [3.3.1] bridged bicyclic phloroglucinol natural products

“…Kraus was able to rapidly test his proposal by first constructing known β-ketoester 113 in three steps via 112 following the work of Rothberg 36 (Scheme 26). To his delight, Snider’s managese(III) cyclization conditions worked nicely to afford the sought after bicyclic core ( 114 ).…”