Synthetic Studies of the Angucycline Antibiotics. Stereocontrolled Assembly of the SF 2315B Ring System

1995 ◽  
Vol 60 (21) ◽  
pp. 6866-6871 ◽  
Author(s):  
Kyungjin Kim ◽  
Yu Guo ◽  
Gary A. Sulikowski
Keyword(s):  
Ring System ◽  
Synthetic Studies ◽  
Angucycline Antibiotics

Synthetic studies related to mycobactins. III. Approaches to the synthesis of the cobactin ring system

1972 ◽  
Vol 25 (11) ◽  
pp. 2429 ◽  
Author(s):  
DSC Black ◽  
RFC Brown ◽  
AM Wade
Keyword(s):  
Primary Amine ◽  
Ring Expansion ◽  
Hydroxamic Acids ◽  
Ring System ◽  
Ethyl Benzoate ◽  
Yield Reduction ◽  
Similar Reaction ◽  
Oxidation Reactions ◽  
Cyclic Hydroxamic Acids ◽  
Synthetic Studies

The synthesis of several seven-membered cyclic hydroxamic acids has been carried out in low yield. Reduction of diethyl 2-hydroxyiminoheptane-l,7-dioate afforded ethyl 1-hydroxy-7-oxohexahydroazepine-2-carboxylate, together with related acyclic products. The cobactin precursor 3-bromo-1-hydroxyhexahydro-azepin-2-one was obtained by the ring expansion of 2-bromocyclohexanone with benzenesulphonohydroxamic acid and also by the peracid oxidation of 6-bromo-7-ethoxy-3,4,5,6-tetrahydro-2H-azepine. The methyl and cinnamyl imidates of hexanolactam were oxidized by peracid to 1-hydroxyhexahydroazepin-2-one, in addition to the related imino- and nitroso-hexanoic esters. In a similar reaction, 1-hydroxypiperidin-2-one was obtained from 2-methoxy-3,4,5,6-tetrahydropyridine. During the course of these oxidation reactions, the intermediate oxaziridines 7-methoxy-8-oxa-1-azabicyclo[5,1,0]octane and 6-bromo-7-ethoxy-8-oxa-1-azabicyclo[5,1,0]octane were isolated and identified. The peraoid oxidation of ethyl N-cyclohexylbenzimidate yielded cyclohexylhydroxylamine and ethyl benzoate in reasonable yields. This reaction suggests a useful method for the conversion of a primary amine into the related hydroxylamine.

Synthetic Studies on Ciguatoxin—Synthesis of H–I–J Ring System

Tetrahedron ◽  
2000 ◽  
Vol 56 (52) ◽  
pp. 10209-10219 ◽  
Author(s):  
Tong-Zhu Liu ◽  
Jian-Min Li ◽  
Minoru Isobe
Keyword(s):  
Ring System ◽  
Synthetic Studies

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

scholarly journals Synthetic Studies on Aphidicolane and Stemodane Diterpenes. III. An Alternative Stereoselective Access to Aphidicolane-Type B/C/D-Ring System.

1994 ◽  
Vol 42 (9) ◽  
pp. 1756-1759 ◽  
Author(s):  
Tetsuaki TANAKA ◽  
Kaszuo MURAKAMI ◽  
Osamu OKUDA ◽  
Takeshi KURODA ◽  
Tetsuya INOUE ◽  
...  
Keyword(s):  
Ring System ◽  
Type B ◽  
Synthetic Studies
Sign in / Sign up

Export Citation Format

Share Document