Recent advances in the total synthesis of cyclobutane-containing natural products

Li, Jinshan; Gao, Kai; Bian, Ming; Ding, Hanfeng

doi:10.1039/c9qo01178a

Cited by 166 publications

(85 citation statements)

References 154 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Equipped with two branched alkyl arms, lithium diisopropylamide (LDA) is especially suited to this role and, consequently, has been one of the most commonly utilised reagents in organic chemistry for 50 years, [20] particularly in natural product syntheses. [21] Although sodium diisopropylamide (NaDA) was first prepared as long ago as 1959, only a decade after its lighter sibling, it has essentially remained unused. In 2017, Collum and co-workers summed it up by remarking that "sodium diisopropylamide has been used in about a dozen studies overall, whereas lithium diisopropylamide is probably used thousands of times daily".…”

Section: The Rise Of Organosodium Mediation In Stoichiometric Organicmentioning

confidence: 99%

Alkali‐Metal Mediation: Diversity of Applications in Main‐Group Organometallic Chemistry

2020

View full text Add to dashboard Cite

show abstract

Section: The Rise Of Organosodium Mediation In Stoichiometric Organicmentioning

confidence: 99%

Alkali‐Metal Mediation: Diversity of Applications in Main‐Group Organometallic Chemistry

2020

View full text Add to dashboard Cite

show abstract

“…Cyclobutanes are also core architectures of pharmaceutics and natural products. 36 Solid-state reactivity using the template strategy has further enabled structural diversification of cyclobutane architectures that has resulted in functional molecular materials with intriguing properties (i.e., multiresponsive solids, 37 chemical patterning, 38 photoactuators 39 ).…”

Section: Discussionmentioning

confidence: 99%

Opportunities Using Boron to Direct Reactivity in the Organic Solid State

Campillo‐Alvarado

MacGillivray

2020

Synlett

View full text Add to dashboard Cite

This Account describes work by our research group that highlights opportunities to utilize organoboron molecules to direct chemical reactivity in the organic solid state. Specifically, we convey a previously unexplored use of hydrogen bonding of boronic acids and boron coordination in boronic esters to achieve [2+2]-photocycloadditions in crystalline solids. Organoboron molecules act as templates or ‘shepherds’ to organize alkenes in a suitable geometry to undergo regio- and stereoselective [2+2]-photocycloadditions in quantitative yields. We also provide a selection of publications that served as an inspiration for our strategies and offer challenges and opportunities for future developments of boron in the field of materials and solid-state chemistry.1 Introduction1.1 Template Strategy for [2+2]-Photocycloadditions in the Solid State2 Boronic Acids as Templates for [2+2]-Photocycloadditions in the Solid State2.1 Supramolecular Catalysis of [2+2]-Photocycloadditions in the Solid State Using Boronic Acids3 Boronic Esters as Templates for [2+2]-Photocycloadditions in the Solid State3.1 Application of Photoproducts: Separation of Thiophene from Benzene through Crystallization3.2 Crystal Reactivity of B←N-Bonded Adducts: The Case of Styrylthiophenes4 Conclusions and Perspectives

show abstract

“…The cyclobutane unit is found as a basic structural element in a wide range of naturally occurring compounds in bacteria, fungi, plants, and marine invertebrates [18,19,[169][170][171][172][173][174]. The chemistry and biochemistry of cyclobutanes is widely described in the scientific literature and is of great interest to chemists and pharmacologists, since many representatives of this class of compounds demonstrate a wide range of biological activities [18,19,73,[175][176][177][178].…”

Section: Cyclobutane Containing Steroids and Triterpenoidsmentioning

confidence: 99%

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

2021

View full text Add to dashboard Cite

This review focuses on the rare group of carbon-bridged steroids (CBS) and triterpenoids found in various natural sources such as green, yellow-green, and red algae, marine sponges, soft corals, ascidians, starfish, and other marine invertebrates. In addition, this group of rare lipids is found in amoebas, fungi, fungal endophytes, and plants. For convenience, the presented CBS and triterpenoids are divided into four groups, which include: (a) CBS and triterpenoids containing a cyclopropane group; (b) CBS and triterpenoids with cyclopropane ring in the side chain; (c) CBS and triterpenoids containing a cyclobutane group; (d) CBS and triterpenoids containing cyclopentane, cyclohexane or cycloheptane moieties. For the comparative characterization of the antitumor profile, we have added several semi- and synthetic CBS and triterpenoids, with various additional rings, to identify possible promising sources for pharmacologists and the pharmaceutical industry. About 300 CBS and triterpenoids are presented in this review, which demonstrate a wide range of biological activities, but the most pronounced antitumor profile. The review summarizes biological activities both determined experimentally and estimated using the well-known PASS software. According to the data obtained, two-thirds of CBS and triterpenoids show moderate activity levels with a confidence level of 70 to 90%; however, one third of these lipids demonstrate strong antitumor activity with a confidence level exceeding 90%. Several CBS and triterpenoids, from different lipid groups, demonstrate selective action on different types of tumor cells such as renal cancer, sarcoma, pancreatic cancer, prostate cancer, lymphocytic leukemia, myeloid leukemia, liver cancer, and genitourinary cancer with varying degrees of confidence. In addition, the review presents graphical images of the antitumor profile of both individual CBS and triterpenoids groups and individual compounds.

show abstract

Recent advances in the total synthesis of cyclobutane-containing natural products

Abstract: Recent developments of strategies on the construction of cyclobutanes and their application in complex natural product synthesis are discussed.

Cited by 166 publications

References 154 publications

Alkali‐Metal Mediation: Diversity of Applications in Main‐Group Organometallic Chemistry

Alkali‐Metal Mediation: Diversity of Applications in Main‐Group Organometallic Chemistry

Opportunities Using Boron to Direct Reactivity in the Organic Solid State

Antitumor Profile of Carbon-Bridged Steroids (CBS) and Triterpenoids

Contact Info

Product

Resources

About