Construction of the Steroid Framework via a Functionalized Macrocyclic Compound

Dyker, Gerald; Grundt, Peter

doi:10.1002/(sici)1099-0690(199901)1999:1<323::aid-ejoc323>3.0.co;2-m

Cited by 14 publications

(1 citation statement)

References 24 publications

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“…Coupled with other transformations, this reaction can initiate domino processes that give annulated ring systems. Pursuing this goal [109][110][111][112][113], Dyker et al devised a double transannular cyclization strategy to access the tetracyclic steroid skeleton in the form of isomeric cis/trans-68 and cis/trans-69, which relied on the intramolecular Heck cyclization of allylic alcohol 65 to form the precursor macrocycle 66 (Figure 12) [114]. In addition to 66, a 26-membered macrocycle 67 was isolated in an unneglectable yield of 17%.…”

Section: Single Double or Multifold Heck Reactionsmentioning

confidence: 99%

Heck Macrocyclization in Forging Non-Natural Large Rings including Macrocyclic Drugs

Cai

Sun

et al. 2023

IJMS

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The intramolecular Heck reaction is a well-established strategy for natural product total synthesis. When constructing large rings, this reaction is also referred to as Heck macrocyclization, which has proved a viable avenue to access diverse naturally occurring macrocycles. Less noticed but likewise valuable, it has created novel macrocycles of non-natural origin that neither serve as nor derive from natural products. This review presents a systematic account of the title reaction in forging this non-natural subset of large rings, thereby addressing a topic rarely covered in the literature. Walking through two complementary sections, namely (1) drug discovery research and (2) synthetic methodology development, it demonstrates that beyond the well-known domain of natural product synthesis, Heck macrocyclization also plays a remarkable role in forming synthetic macrocycles, in particular macrocyclic drugs.

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