A New Synthetic Approach to (+)-Hyacinthacine A1and the First Total Synthesis and Absolute Configuration Assignment of Naturally Occurring (+)-Hyacinthacine A6

2007 ◽  
Vol 2007 (36) ◽  
pp. 6078-6083 ◽  
Author(s):  
Isidoro Izquierdo ◽  
María T. Plaza ◽  
Juan A. Tamayo ◽  
Fernando Sánchez-Cantalejo
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Synthetic Approach ◽  
Naturally Occurring ◽  
Configuration Assignment

ChemInform Abstract: Total Synthesis and Determination of the Absolute Configuration of FD-838, a Naturally Occurring Azaspirobicyclic Product.

ChemInform ◽  
2009 ◽  
Vol 40 (47) ◽  
Author(s):  
Yujiro Hayashi ◽  
Kuppusamy Sankar ◽  
Hayato Ishikawa ◽  
Yuriko Nozawa ◽  
Kazutoshi Mizoue ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Naturally Occurring ◽  
The Absolute

scholarly journals Total Syntheses of Pladienolide-Derived Spliceosome Modulators

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5938
Author(s):  
Jaehoon Sim ◽  
Eunbin Jang ◽  
Hyun Jin Kim ◽  
Hongjun Jeon
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Structural Features ◽  
Synthetic Approach ◽  
Synthetic Analog ◽  
Phase I Clinical Trials ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Anti Cancer ◽  
Synthetic Approaches

Pladienolides, an emerging class of naturally occurring spliceosome modulators, exhibit interesting structural features, such as highly substituted 12-membered macrocycles and epoxide-containing diene side chains. The potential of pladienolides as anti-cancer agents is confirmed by H3B-8800, a synthetic analog of this natural product class, which is currently under Phase I clinical trials. Since its isolation in 2004 and the first total synthesis in 2007, a dozen total syntheses and synthetic approaches toward the pladienolide class have been reported to date. This review focuses on the eight completed total syntheses of naturally occurring pladienolides or their synthetic analogs, in addition to a synthetic approach to the main framework of the natural product.

Concise Total Synthesis of (+)-Atlanticone C

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1598-1602 ◽  
Author(s):  
Thorsten Bach ◽  
Johanna Proessdorf ◽  
Andreas Zech ◽  
Christian Jandl
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Photochemical Reaction ◽  
Enantioselective Total Synthesis ◽  
Naturally Occurring ◽  
The Absolute

The first enantioselective total synthesis of (+)-atlanticone C is described. The complex tricyclic protoilludane core was rapidly assembled by a photochemical reaction cascade starting from an easily accessible indanone precursor (3 steps). Optimization of an enantioselective Corey–Bakshi–Shibata reduction permitted a catalytic chiral reso­lution of the racemic photoproduct (45% over two steps; up to 98% ee). The enantiomerically enriched photoproduct was efficiently transformed into the (+)-enantiomer of atlanticone C (10 steps; 18% yield), and the absolute configuration of naturally occurring (–)-atlanticone C was thereby determined.

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