Recent advances in the application of Diels–Alder reactions involving o-quinodimethanes, aza-o-quinone methides and o-quinone methides in natural product total synthesis

2018 ◽  
Vol 47 (21) ◽  
pp. 7926-7953 ◽  
Author(s):  
Baochao Yang ◽  
Shuanhu Gao
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Organic Synthesis ◽  
Diels Alder ◽  
Quinone Methides ◽  
Recent Advances

This review summarizes recent advances in Diels–Alder reactions involving o-QDMs, o-QMs and aza-o-QMs. The power and potential of this strategy in organic synthesis and natural product total synthesis is highlighted.

scholarly journals The Total Synthesis of (–)-Scabrolide a

2020 ◽  
Author(s):  
Nicholas Hafeman ◽  
Steven A. Loskot ◽  
Chris Reimann ◽  
Beau P. Pritchett ◽  
Scott C. Virgil ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

The first total synthesis of the norcembranoid diterpenoid scabrolide A is disclosed. The route begins with the synthesis of two chiral pool-derived fragments, which undergo a convergent coupling to expediently introduce all 19 carbon atoms of the natural product. An intramolecular Diels–Alder reaction and an enone-olefin cycloaddition/fragmentation sequence are then employed to construct the fused [5–6–7] linear carbocyclic core of the molecule and to complete the total synthesis.

Recent advances in the synthesis of oxaspirolactones and their application in the total synthesis of related natural products

2019 ◽  
Vol 17 (31) ◽  
pp. 7270-7292 ◽  
Author(s):  
Sagar S. Thorat ◽  
Ravindar Kontham
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Medicinal Chemistry ◽  
Natural Product Chemistry ◽  
Structural Motifs ◽  
Recent Advances ◽  
Synthetic Molecules ◽  
Product Chemistry

Oxaspirolactones are ubiquitous structural motifs found in natural products and synthetic molecules with a diverse biochemical and physicochemical profile, and represent a valuable target in natural product chemistry and medicinal chemistry.

Diels-Alder Cascades in Natural Product Total Synthesis

2018 ◽  
pp. 159-189
Author(s):  
Richard P. Hsung ◽  
Zhi-Xiong Ma ◽  
Lichao Fang ◽  
John B. Feltenberger
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Diels Alder

Intramolecular Diels-Alder Cycloadditions of cis-Cyclohexadienediols Derived Enzymatically from (2-Azidoethyl)benzene. Construction of Highly Functionalized Bridged Isoquinoline Synthons

2001 ◽  
Vol 66 (8) ◽  
pp. 1269-1286 ◽  
Author(s):  
Josef Zezula ◽  
Tomáš Hudlický ◽  
Ion Ghiviriga
Keyword(s):  
Methyl Ester ◽  
Maleic Anhydride ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Diels Alder

(3aR,7aS)-4-(2-Azidoethyl)-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole (22) was converted in two steps to trienes23and24, which upon heating underwent intramolecular Diels-Alder reactions to give mixtures of isomeric 11,11-dimethyl-5-oxo-10,12-dioxa-4-azatetracyclo[6.5.2.01,6.09,13]pentadec-14-ene-7-carboxylates25,26and27,28, respectively. These products were separated and identified. For comparison, intermolecular Diels-Alder cycloaddition of diene22with maleic anhydride was carried out. Products of this reaction, 1-(2-azidoethyl)-4,4-dimethyl-3,5,10-trioxatetracyclo[5.5.2.02,6.08,12]tetradec-13-ene-9,11-diones (29and30) were converted to methyl ester analogues of31and32in a two-step sequence. The stereochemical outcome of these cycloadditions is discussed as well as their possible utilization in organic synthesis, especially in total synthesis of some alkaloids.

scholarly journals Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1199
Author(s):  
Sijia Chen ◽  
Chongguo Jiang ◽  
Nan Zheng ◽  
Zhen Yang ◽  
Lili Shi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Organic Synthesis ◽  
Total Syntheses

Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five years. Additionally, the hetero-Pauson-Khand reaction in the synthesis of heterocycles will also be discussed. Focusing on the panorama of organic synthesis, this review highlights the strategically developed Pauson-Khand reaction in fulfilling total synthetic tasks and its synthetic attractiveness is aimed to be illustrated.

ChemInform Abstract: Recent Advances of Desymmetrization Protocol Applied in Natural Product Total Synthesis

ChemInform ◽  
2015 ◽  
Vol 46 (9) ◽  
pp. no-no
Author(s):  
Ming Wang ◽  
Minghao Feng ◽  
Bingqing Tang ◽  
Xuefeng Jiang
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Recent Advances

Recent Advances in Steroid Synthesis: A Tribute to Sir Derek Barton

2018 ◽  
Vol 71 (9) ◽  
pp. 627
Author(s):  
Kieran D. Jones ◽  
Scott G. Stewart
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Methyl Ether ◽  
Ring System ◽  
Natural Product Synthesis ◽  
Steroid Synthesis ◽  
Research Areas ◽  
Recent Advances

The synthesis of steroids and gaining an ultimate understanding of their reactivity was one of Sir Derek Barton’s most notable research areas. This highlight will focus on the construction of the steroid ring system from 2016 to 2018, and will include pathways that eventually led to natural product synthesis. For example, efficient syntheses of ent-pregnanolone sulfate and oestradiol methyl ether will be explained along with the total synthesis of cannogenol-3-O-α-l-rhamnoside.

Recent Advances in Natural Product Synthesis by Using Intramolecular Diels−Alder Reactions†

2005 ◽  
Vol 105 (12) ◽  
pp. 4779-4807 ◽  
Author(s):  
Ken-ichi Takao ◽  
Ryosuke Munakata ◽  
Kin-ichi Tadano
Keyword(s):  
Natural Product ◽  
Diels Alder ◽  
Natural Product Synthesis ◽  
Recent Advances
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