Synthetic Studies on Cyclocitrinol: Construction of the ABC Ring System Based on Epoxy-Nitrile Cyclization

Synlett ◽  
2020 ◽  
Author(s):  
Kazuto Sato ◽  
Keiji Tanino
Keyword(s):  
Intramolecular Cyclization ◽  
Ring Opening ◽  
Model Compound ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Cyclization Reaction ◽  
Ring Opening Reaction ◽  
Synthetic Studies ◽  
Highly Strained

The stereoselective synthesis of a model compound containing the ABC ring system of cyclocitrinol was accomplished. After connecting a C-ring allyltitanium segment with an A ring bicyclo[4.1.0]heptanone segment, the seven-membered B ring moiety was constructed by an intramolecular cyclization reaction of an epoxy nitrile. The enone moiety was introduced through an oxidative decyanation reaction, and the bicyclo[4.4.1]undecane skeleton with the highly strained olefin moiety was formed through a ring-opening reaction of the bicyclo[4.1.0]heptane substructure.

ChemInform Abstract: Synthetic Studies on Maitotoxin. Part 2. Stereoselective Synthesis of the WXYZA′-Ring System.

ChemInform ◽  
2008 ◽  
Vol 39 (30) ◽  
Author(s):  
Masayuki Morita ◽  
Tasuku Haketa ◽  
Hiroyuki Koshino ◽  
Tadashi Nakata
Keyword(s):  
Stereoselective Synthesis ◽  
Ring System ◽  
Synthetic Studies

ChemInform Abstract: Synthetic Studies on Brevetoxin-B. Part 3. Stereoselective Synthesis of the IJK-Ring System.

ChemInform ◽  
2000 ◽  
Vol 31 (51) ◽  
pp. no-no
Author(s):  
Hiroko Matsukura ◽  
Nobuyuki Hori ◽  
Goh Matsuo ◽  
Tadashi Nakata
Keyword(s):  
Stereoselective Synthesis ◽  
Ring System ◽  
Synthetic Studies

scholarly journals Stereoselective Synthesis of 4-O-Tosyltetrahydropyrans via Prins Cyclization Reaction of Enol Ethers

SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 36-45
Author(s):  
Sujit Sarkar ◽  
Namita Devi ◽  
Bikoshita Porashar ◽  
Santu Ruidas ◽  
Anil Saikia
Keyword(s):  
Intramolecular Cyclization ◽  
Stereoselective Synthesis ◽  
Cyclization Reaction ◽  
Prins Cyclization ◽  
Enol Ethers ◽  
Toluenesulfonic Acid

Intramolecular cyclization of enol ethers mediated by para-toluenesulfonic acid leads to substituted tetrahydropyrans in good to moderate yields. The reaction is diastereoselective.

ChemInform Abstract: Synthetic Studies on Aplysiatoxin. Intramolecular Ester Formation from 3-Acetoxyfuran Derivative via Oxidative Ring Opening Reaction.

ChemInform ◽  
2010 ◽  
Vol 22 (44) ◽  
pp. no-no
Author(s):  
K. OKADA ◽  
M. MIZUNO ◽  
H. SASAKI ◽  
K. SUGIURA ◽  
H. TANINO ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reaction ◽  
Ester Formation ◽  
Synthetic Studies

Cyclophanes. VI. The synthesis of [2,2](3,3')biphenylparacyclophanedienes

1976 ◽  
Vol 29 (6) ◽  
pp. 1267 ◽  
Author(s):  
PJ Jessup ◽  
JA Reiss
Keyword(s):  
Ring Opening ◽  
Ring System ◽  
Ring Contraction ◽  
Stevens Rearrangement ◽  
Ring Opening Reaction ◽  
Disubstituted Benzene ◽  
Contraction Procedure

The preparations of [2,2](3,3')biphenylparacyclophane-1,9-dine (19) and a dimethyl derivative (20) synthesized by a ring-contraction procedure of the corresponding dithiacyclophanes (11) and (12) are reported. Both dienes (19) and (20) photocyclized under oxidative conditions to the benzo[ghi]- perylenes (21) and (22). Difficulties associated with the Stevens rearrangement in cyclophanes containing a para-disubstituted benzene moiety have been rationalized in terms of a competing ring- opening reaction. Several other reactions of the biphenylparacylophane ring system are reported, and the stereochemistry of the macrocycle is discussed.

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