ChemInform Abstract: Highly Efficient Synthesis of the Natural Spiro‐Terpenoid (.+‐.)‐ Andirolactone (I).

Orduña, Arturo; Zepeda, L. Gerardo; Tamariz, Joaquı́n

doi:10.1002/chin.199339264

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“…Another synthesis of spiro‐terpenoid (±)‐andirolactone has been reported from the reaction of diacetyl and 4‐nitrobenzoyl chloride in five steps (Scheme ) …”

Section: Natural Products and Biological Active Motifs With Spirobutementioning

confidence: 99%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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“…Another synthesis of spiro‐terpenoid (±)‐andirolactone has been reported from the reaction of diacetyl and 4‐nitrobenzoyl chloride in five steps (Scheme ) …”

Section: Natural Products and Biological Active Motifs With Spirobutementioning

confidence: 99%