Application of Ring Closing Metathesis to the First Total Synthesis of (R)-(+)-Muscopyridine:  Determination of Absolute Stereochemistry

2000 ◽  
Vol 65 (21) ◽  
pp. 7231-7234 ◽  
Author(s):  
Hisahiro Hagiwara ◽  
Tomoko Katsumi ◽  
Vijayendra P. Kamat ◽  
Takashi Hoshi ◽  
Toshio Suzuki ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Closing Metathesis ◽  
Absolute Stereochemistry

scholarly journals Synthetic study of ravidomycin, a hybrid natural product

2000 ◽  
Vol 72 (9) ◽  
pp. 1783-1786 ◽  
Author(s):  
Keisuke Suzuki
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Amino Sugar ◽  
Antitumor Antibiotics ◽  
Ready Availability ◽  
Silyl Acetals ◽  
Gilvocarcin V ◽  
Absolute Stereochemistry

Strategies and tactics associated with the total synthesis of hybrid natural products are discussed. The target is ravidomycin (2), one of the gilvocarcin-class antitumor antibiotics with an aryl C-glycoside structure. The first total synthesis of 2, which was achieved along similar lines of that of gilvocarcin V (1), served for the determination of the relative as well as the absolute stereochemistry of 2. Also revealed was a limitation of the synthetic scheme so long as the amino sugar congener was concerned. A preliminary result is discussed on the [2+2+2] approach that relies on the ready availability of various benzocyclobutene derivatives via regioselective [2+2] cycloaddition of α-alkoxybenzynes and ketene silyl acetals.

ChemInform Abstract: The First Enantioselective Total Synthesis of Cyclomyltaylane-5α-ol and Determination of Its Absolute Stereochemistry.

ChemInform ◽  
2010 ◽  
Vol 33 (30) ◽  
pp. no-no
Author(s):  
Hisahiro Hagiwara ◽  
Hitoshi Sakai ◽  
Takashi Uchiyama ◽  
Yoshiaki Ito ◽  
Noriyuki Morita ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis ◽  
Absolute Stereochemistry

Total synthesis and determination of the absolute stereochemistry of the squalene synthase inhibitors CJ-13,981 and CJ-13,982

2009 ◽  
Vol 50 (26) ◽  
pp. 3388-3390 ◽  
Author(s):  
Frederick Calo ◽  
Alexander Bondke ◽  
Jeffery Richardson ◽  
Andrew J.P. White ◽  
Anthony G.M. Barrett
Keyword(s):  
Total Synthesis ◽  
Squalene Synthase ◽  
The Absolute ◽  
Absolute Stereochemistry

Total Synthesis of (−)-Stellettamide B and Determination of Its Absolute Stereochemistry

2001 ◽  
Vol 3 (2) ◽  
pp. 193-196 ◽  
Author(s):  
Naoki Yamazaki ◽  
Wataru Dokoshi ◽  
Chihiro Kibayashi
Keyword(s):  
Total Synthesis ◽  
Absolute Stereochemistry

scholarly journals Evolution of the Total Syntheses of Batzellasides the First Marine Piperidine Iminosugar

2013 ◽  
Vol 8 (7) ◽  
pp. 1934578X1300800
Author(s):  
Tetsuya Sengoku ◽  
Jolanta Wierzejska ◽  
Masaki Takahashi ◽  
Hidemi Yoda
Keyword(s):  
Total Synthesis ◽  
First Generation ◽  
Ring System ◽  
Piperidine Ring ◽  
Total Syntheses ◽  
Asymmetric Dihydroxylation ◽  
Biological Studies ◽  
The Common ◽  
Absolute Stereochemistry

Batzellasides A-C are C-alkylated piperidine iminosugars isolated from a sponge Batzella sp. The first total synthesis of (+)-batzellaside B was achieved by employing a chiral pool approach starting from L-arabinose for the construction of a piperidine ring system. Subsequently a practical second-generation synthesis was developed by utilizing a Sharpless asymmetric dihydroxylation for the preparation of the common piperidine intermediate elaborated in the first-generation synthesis. The overall yield of batzellaside B was improved to 3.3% by introducing the exocyclic C8 stereocenter via facial selective hydride addition to a linear ketone. These syntheses allowed for the determination of the absolute stereochemistry of this natural product as well as for providing precious samples which would pave the way for further biological studies.

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