https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.

Cascade reactions in total synthesis.

The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Diels-Alder cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder's birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.

https://www.ch.ic.ac.uk/local/organic/pericyclic/DA.pdf

The Diels--Alder reaction in total synthesis.

The asymmetric intramolecular Heck reaction in natural product total synthesis.

A CD method for determination of the absolute stereochemistry of acyclic glycols. 1. Application of the CD exciton chirality method to acyclic 1,3-dibenzoate systems

Total synthesis of (+)-halenaquinol and (+)-halenaquinone. Experimental proof of their absolute stereostructures theoretically determined

An efficient preparation procedure of optically pure Wieland-Miescher ketone, (8aR)-(−)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione (1), is described, and its absolute stereochemistry is confirmed by the application of the CD exciton chirality method to its derivatives

Efficient Preparation of Optically Pure Wieland-Miescher Ketone and Confirmation of Its Absolute Stereochemistry by the CD Exciton Chirality Method

The first total synthesis of (+)-xestoquinone 1, a biologically active marine natural product isolated from tropical marine sponges, was achieved. Therefore, the absolute stereochemistry of (+)-xestoquinone 1 was determined to be 12bS. Finally, xestoquinone (12bS)-(+)-1 was converted to xestoquinol (12bS)-2, although xestoquinol 2 itself has not been isolated yet as a natural product. The absolute configuration of xestoquinone 1 was also established by the comparison of the CD spectrum of naphthalene-diene derivative 22 with the theoretically calculated CD curve of a model compound (12bS)-23

Total synthesis and absolute stereochemistry of (+)-xestoquinone and xestoquinol

Adiciaquinones A (+)-1 and B (+)-2 were synthesized and their absolute configurations were determined to be (14bS).

Takeo Kuriki

Papers

A CD method for determination of the absolute stereochemistry of acyclic glycols. 1. Application of the CD exciton chirality method to acyclic 1,3-dibenzoate systems

Total synthesis of (+)-halenaquinol and (+)-halenaquinone. Experimental proof of their absolute stereostructures theoretically determined

Efficient Preparation of Optically Pure Wieland-Miescher Ketone and Confirmation of Its Absolute Stereochemistry by the CD Exciton Chirality Method

Total synthesis and absolute stereochemistry of (+)-xestoquinone and xestoquinol

Synthesis and absolute stereochemistry of (+)-adociaquinones A and B