Application of Claisen Rearrangement and Olefin Metathesis in Organic Synthesis

Abstract

Several new synthetic methods to diverse polycycles and heterocycles on the basis of [3,3]-sigmatropic rearrangement and ring-closing metathesis as key steps are summarized. In this regard, Claisen, aza-Claisen, and Overman rearrangements are used in combination with other popular reactions such as ring-closing metathesis, Suzuki coupling, Diels-Alder reaction, and retro-Diels-Alder reaction. To this end, we prepared polycycles (e.g., cyclophanes, cage molecules), heterocycles (e.g., oxepins, azapins), carbocycles, and spirocycles with the use of the above protocol.

Synthesis of Unusual Amino Acid Derivatives Containing Bicyclo[2.2.2]octane Unit by the Diels‐Alder Approach Involving Pentacene

“…In view of our interest and the importance of BCO unit and the role of unusual AAAs in drug design we considered the synthesis of unusual AAA derivatives containing BCO unit by Diels‐Alder reaction. Anthracene [33–36] undergo Diels‐Alder reaction and the higher analogue of anthracene such as pentacene was chosen as possible diene and dienophiles containing AAA building block are prepared from serine derivatives as starting materials. To realize the strategy, we began our journey with the preparation of different dienophiles from serine.…”

Selectivity: A Goal for Synthetic Economy

“…Next, when the mono-allyl derivative 119 was treated with an allyl Grignard reagent, the diallyl dihydroxy derivative 120 was obtained (Scheme 25 ). 35…”

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

“…In addition to these cyclophanes, the anthracenophane derivatives seem to be worthy candidates for further synthetic investigation. To this end, 1,6‐diketo[6](9,10)anthracenophane ( 96 ) was identified as a target molecule involving a simple synthetic sequence based on RCM as a key step . The required dione 88 has been prepared by following the literature procedure .…”