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Galiellalactone: a review on synthetic strategies and tactics

Sovan Dey, Arindam Das, and Md. Firoj Hossain

Department of Chemistry, University of North Bengal, Raja Rammohunpur, Darjeeling, India

 

E-mail: firoj01982@nbu.ac.in

Received: 14 April 2022  Accepted: 10 December 2022

Abstract:

(–)-Galiellalactone is a secondary fungal metabolite. It was found from dead wood in Chile and first isolated from ascomycetes Galiella rufa (strain A75-86) and A111-95. It has unique architecture. This molecule consists of [5,5,6]-fused tricyclic ring system. The α,β-unsaturated lactone ring present in (–)-galiellalactone acts as Michael acceptor. It has four stereocenters. The tertiary stereocenter has the angular hydroxyl group, which is very important for its bioactivity. This fungal metabolite shows different bioactivities like anti-tumor, anti-inflammatory, anti-HIV, and anti-cancer activities. The unique structural feature along with its excellent bioactivities encouraged us to write this review article. This review comprises the different synthetic approaches with the beauty and uniqueness of various reactions like intramolecular Diels–Alder reaction and Metathesis. Herein, we have discussed the syntheses for the molecule (–)-galiellalactone and its stereoisomers available to date.

Keywords: Desoxygaliellalactone; Diels–Alder reaction; Galiellalactone; Metathesis; Pregaliellalactone

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02630-1

 

Chemical Papers 77 (5) 2329–2342 (2023)

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