The use of photochemical transformations is a powerful strategy that allows for the formation of a high degree of molecular complexity from relatively simple building blocks in a single step. A central feature of all light-promoted transformations is the involvement of electronically excited states, generated upon absorption of photons. This produces transient reactive intermediates and significantly alters the reactivity of a chemical compound. The input of energy provided by light thus offers a means to produce strained and unique target compounds that cannot be assembled using thermal protocols. This review aims at highlighting photochemical transformations as a tool for rapidly accessing structurally and stereochemically diverse scaffolds. Synthetic designs based on photochemical transformations have the potential to afford complex polycyclic carbon skeletons with impressive efficiency, which are of high value in total synthesis.

Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis

Photochemical reactions contribute in a significant way to the existing repertoire of carbon-carbon bond-forming reactions by allowing access to exceptional molecular structures that cannot be obtained by conventional means. In this Review, the most important photochemical transformations that have been employed in natural product synthesis are presented. Selected total syntheses are discussed as examples, with particular attention given to the photochemical key step and its stereoselectivity. The structural relationship between the photochemically generated molecule and the natural product is shown, and, where necessary, the consecutive reactions in the synthesis are illustrated and classified.

Photochemical reactions as key steps in natural product synthesis

Hypervalent iodine-mediated phenol dearomatization in natural product synthesis

Applications of NMR Spectroscopy in Organic Chemistry.

Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Progress in the construction of cyclooctanoid systems: new approaches and applications to natural product syntheses.

Hybrid systems are constructs of different molecular entities, natural or unnatural, to generate functional molecules in which the characteristics of various components are modulated, amplified or give rise to entirely new properties. These hybrids can be designed from carefully selected components either through domain integration of key structural/ functional features or via straightforward covalent linkages. Some of the recently reported hybrid systems based on steroid, carbohydrate, C60-fullerene platforms, amongst others, mainly crafted with the object of enhancement of the therapeutical spectrum, will be discussed.

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Hybrid systems through natural product leads: An approach towards new molecular entities

Spiroepoxycyclohexa-2,4-dienones in Organic Synthesis

Recent approaches towards synthesis of cis-decalins

Intramolecular Diels–Alder reaction in 1-oxaspiro[2.5]octa-5,7-dien-4-one and sigmatropic shifts in excited states: novel route to sterpuranes and linear triquinanes: formal total synthesis of (±)-coriolin

Vishwakarma Singh

Papers

Progress in the construction of cyclooctanoid systems: new approaches and applications to natural product syntheses.

Hybrid systems through natural product leads: An approach towards new molecular entities

Spiroepoxycyclohexa-2,4-dienones in Organic Synthesis

Recent approaches towards synthesis of cis-decalins

Intramolecular Diels–Alder reaction in 1-oxaspiro[2.5]octa-5,7-dien-4-one and sigmatropic shifts in excited states: novel route to sterpuranes and linear triquinanes: formal total synthesis of (±)-coriolin