Stereoselective Oxidative Dimerization of (1R)-Camphor. A Short Synthesis ofexo,exo‘-3,3‘-Biisoborneol

1999 ◽  
Vol 64 (14) ◽  
pp. 5312-5314 ◽  
Author(s):  
James McNulty ◽  
Monte J. Millar ◽  
Gérald Bernardinelli ◽  
Charles W. Jefford
2019 ◽  
Author(s):  
Lars Gnägi ◽  
Severin Vital Martz ◽  
Daniel Meyer ◽  
Robin Marc Schärer ◽  
Philippe Renaud

<div><div><div><div><p>A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows to achieve a high trans diastereoselectivity during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis require six product purifications and it provides (+)-brefeldin C in 18% overall yield.</p></div></div></div></div>


2019 ◽  
Vol 16 (12) ◽  
pp. 931-934 ◽  
Author(s):  
Alexandra Kamlah ◽  
Franz Bracher

: A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5- dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.


ChemInform ◽  
2010 ◽  
Vol 29 (18) ◽  
pp. no-no
Author(s):  
K. TAKEDA ◽  
N. OHKAWA ◽  
K. HORI ◽  
T. KOIZUMI ◽  
E. YOSHII

1996 ◽  
Vol 37 (11) ◽  
pp. 1885-1888 ◽  
Author(s):  
A.J. Bloodworth ◽  
Brian D Bothwell ◽  
Andrew N Collins ◽  
Nicola L Maidwell

ChemInform ◽  
2010 ◽  
Vol 41 (10) ◽  
Author(s):  
Hanumant B. Borate ◽  
Sangmeshwer P. Sawargave ◽  
Suleman R. Maujan
Keyword(s):  

1998 ◽  
Vol 39 (37) ◽  
pp. 6695-6698 ◽  
Author(s):  
Gebhard Haberhauer ◽  
Rolf Gleiter

SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0138-0142 ◽  
Author(s):  
Azim Halimehjani ◽  
Yazdanbakhsh Nosood ◽  
Shaghayegh Didaran ◽  
Fezzeh Aryanasab

A facile and efficient protocol for the synthesis of 3,5-bis-mercapto-1,2,4-thiadiazoles by the oxidative dimerization of S-alkyl dithiocarbamates using periodic acid as an inexpensive and commercially available oxidant is reported. High to excellent yields and short reaction times are the main advantages of this procedure.


1977 ◽  
Vol 42 (6) ◽  
pp. 948-952 ◽  
Author(s):  
David L. Coffen ◽  
David A. Katonak ◽  
Nels R. Nelson ◽  
Fred D. Sancilio
Keyword(s):  

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