Stereoselective Allylation of 4-Oxoazetidine-2-carbaldehydes. Application to the Stereocontrolled Synthesis of Fused Tricyclic β-Lactams via Intramolecular Diels−Alder Reaction of 2-Azetidinone-Tethered Trienes†

2000 ◽  
Vol 65 (11) ◽  
pp. 3310-3321 ◽  
Author(s):  
Benito Alcaide ◽  
Pedro Almendros ◽  
Nati R. Salgado
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis

Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels–Alder reaction of β,γ-unsaturated α-keto esters

2015 ◽  
Vol 13 (21) ◽  
pp. 5875-5879 ◽  
Author(s):  
Takashi Otani ◽  
Yumiko Tamai ◽  
Kazunori Seki ◽  
Tomohiro Kikuchi ◽  
Taiichiro Miyazawa ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Controlled Synthesis ◽  
Keto Esters ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis

Stereocontrolled synthesis of polyheterocycles via the diene-transmissive hetero Diels–Alder reaction of β,χ-unsaturated α-keto esters is described.

First hetero-diels-alder reaction of an enantiopure 2-sulfinylbuta-1, 3-diene: mild and effective stereocontrolled synthesis of pyranoid derivatives

1997 ◽  
Vol 8 (17) ◽  
pp. 2989-2995 ◽  
Author(s):  
Maria C. Aversa ◽  
Anna Barattucci ◽  
Paola Bonaccorsi ◽  
Giuseppe Bruno ◽  
Placido Giannetto ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis

Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6] tricycles. Part I. Transannular Diels–Alder reactions of 14-membered macrocycles containing trans-dienophiles

1993 ◽  
Vol 71 (8) ◽  
pp. 1152-1168 ◽  
Author(s):  
Yao-Chang Xu ◽  
Andrew L. Roughton ◽  
Raymond Plante ◽  
Solo Goldstein ◽  
Pierre Deslongchamps
Keyword(s):  
Natural Products ◽  
Alder Reaction ◽  
Diels Alder ◽  
Methyl Substituent ◽  
Dimethyl Malonate ◽  
General Methodology ◽  
Racemic Form ◽  
Diels Alder Reaction ◽  
Tricyclic Compounds ◽  
Stereocontrolled Synthesis

Transannular Diels–Alder reactions of 14-membered macrocyclic trienes possessing a methyl substituent on both the diene and dienophile moiety have been investigated. Macrocyclic structures 1a, 1b, and 1c having cis-trans-trans (CTT), trans-cis-trans (TCT), and trans-trans-trans (TTT) geometries could be stereoselectively constructed by coupling appropriately functionalized dienes 5 and dienophile 4 following an intramolecular displacement of an allylic halide by the anion of an appropriately located dimethyl malonate unit. The transannular Diels–Alder reaction performed on 1a led to a mixture of four major tricyclic products, including 34 possessing the unexpected trans-anti-cis (TAC) stereochemistry. When heated at 300 °C, macrocycle 1b underwent an unique conversion via an ene–retroene, Diels–Alder process, producing the unexpected tricycle 41 (racemic form) containing five contiguous chiral centers. A rationale for the above experimental facts is presented. In contrast to the previous results, the transannular Diels–Alder reaction of macrocycle 1c was straightforward, producing a 95% isolated yield of trans-anti-cis (TAC) tricycle 34. This investigation demonstrates a general methodology for the stereocontrolled synthesis of 1,2-dimethyl A.B.C[6.6.6] tricyclic compounds, which are potential precursors to polycyclic natural products such as steroids and terpenes.

Concise Stereocontrolled Synthesis of an α-Carbagalactose Segment of RCAI-56, a Candidate Anticancer Agent

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 977-981
Author(s):  
Naoki Ushida ◽  
Nobukazu Nagai ◽  
Masaatsu Adachi ◽  
Toshio Nishikawa
Keyword(s):  
T Cells ◽  
Antitumor Activity ◽  
Anticancer Agent ◽  
Natural Killer T Cells ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis ◽  
Killer T Cells ◽  
Stimulation Of

RCAI-56 is a synthetic glycolipid exhibiting a potent antitumor activity by stimulation of natural killer T cells. Tetra-O-benzyl-α-carbagalactose, an important synthetic segment of RCAI-56, was stereoselectively synthesized from 1,4-dichloro-2-butene in nine steps, including the key step of organocatalytic asymmetric Diels–Alder reaction between acrolein and 1-benzyloxybutadiene.

Highly stereocontrolled synthesis of (±)-3-oxosilphinene via intramolecular Diels–Alder reaction

1986 ◽  
Vol 0 (9) ◽  
pp. 671-672 ◽  
Author(s):  
Masataka Ihara ◽  
Akihiro Kawaguchi ◽  
Masotoshi Chihiro ◽  
Keiichiro Fukumoto ◽  
Tetsuji Kametani
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Stereocontrolled Synthesis
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