The growing importance of cascade reactions reflects and imparts advances in the state of the art of organic synthesis and underscores the desire of synthetic chemists to achieve higher levels of elegance and efficiency. Besides their aesthetic appeal, cascade processes offer economical and environmentally friendly means for generating molecular complexity. Because of their many advantages, these reactions have found numerous applications in the synthesis of complex molecules, both natural and designed. In this Tutorial Review, we highlight the design and execution of cascade reactions within the context of total synthesis as demonstrated with selected examples from these laboratories.

Abyssomicin C is a recently discovered antibiotic with promising antibacterial activity, high structural complexity, and a novel mechanism of action. We give an account of our abyssomicin campaign and some of the discoveries that were borne of our total synthesis efforts, including a new Lewis acid-templated Diels-Alder reaction, the previously undescribed atrop-abyssomicin C, a facile Brønsted acid-catalyzed isomerization of abyssomicin C, and clarification of the likely biosynthetic origin of abyssomicin D.

A bio-inspired investigation of the reactions of substrates of type 1 with VOF3 and PIFA [phenyliodine(III) bis(trifluoroacetate)] led to a collection of colchicine-like compounds 2–5 and related systems. Biological evaluation revealed that some of the synthesized products had significant cytotoxic properties against the colon cancer cell line HT-29.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.