ChemInform Abstract: Two-Phase Terpene Total Synthesis: Historical Perspective and Application to the Taxol® Problem

ChemInform ◽  
2010 ◽  
Vol 41 (40) ◽  
pp. no-no
Author(s):  
Yoshihiro Ishihara ◽  
Phil S. Baran
Keyword(s):  
Total Synthesis ◽  
Historical Perspective ◽  
Two Phase

scholarly journals Two-Phase Terpene Total Synthesis: Historical Perspective and Application to the Taxol® Problem

Synlett ◽  
2010 ◽  
Vol 2010 (12) ◽  
pp. 1733-1745 ◽  
Author(s):  
Phil Baran ◽  
Yoshihiro Ishihara
Keyword(s):  
Total Synthesis ◽  
Historical Perspective ◽  
Two Phase

ChemInform Abstract: Methyl Epijasmonate: Historical Perspective and Total Synthesis

ChemInform ◽  
2000 ◽  
Vol 31 (40) ◽  
pp. no-no
Author(s):  
Tarun K. Sarkar ◽  
Binay K. Ghorai
Keyword(s):  
Total Synthesis ◽  
Historical Perspective

scholarly journals Asymmetric Synthesis of Quinine: A Landmark in Organic Synthesis

2006 ◽  
Vol 1 (10) ◽  
pp. 1934578X0600101 ◽  
Author(s):  
Vijay Nair ◽  
Rajeev S. Menon ◽  
Sreekumar Vellalath
Keyword(s):  
Organic Chemistry ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Chemical Industry ◽  
Crucial Role ◽  
Historical Perspective ◽  
Modern Medicine ◽  
Present Review ◽  
Catalytic Asymmetric Synthesis

Ever since its isolation in 1820, Quinine has played a crucial role in the development of organic chemistry, the chemical industry and modern medicine. A total synthesis of quinine, widely regarded as an event of epochal importance, was claimed by Woodward and Doering in 1945. This work, however, heavily relied on unsubstantiated literature reports and it appears that Woodward's work fell short of a total synthesis of quinine. The first total synthesis of quinine was reported by Uskokovic in the 1970s. The first stereoselective total synthesis of quinine was accomplished only in 2001, by Stork, who incidentally is the originator of the concept of stereoselectivity in total synthesis. Apart from the stereoselectivity, Stork's synthesis of quinine is remarkable for its conceptual uniqueness and retrosynthetic novelty. Naturally, this work has been attested as a landmark in organic synthesis by leaders in the field. Subsequently, Jacobson and Kobayashi reported the catalytic asymmetric synthesis of quinine in 2003 and 2004, respectively. Both these synthesis have followed a similar approach. The present review has attempted to provide a concise account of the synthesis of quinine from a historical perspective.

scholarly journals Two-Phase Total Synthesis of Taxanes: Tactics and Strategies

2020 ◽  
Vol 85 (16) ◽  
pp. 10293-10320
Author(s):  
Yuzuru Kanda ◽  
Yoshihiro Ishihara ◽  
Nathan C. Wilde ◽  
Phil S. Baran
Keyword(s):  
Total Synthesis ◽  
Two Phase

14-Step Synthesis of (+)-Ingenol from (+)-3-Carene

Science ◽  
2013 ◽  
Vol 341 (6148) ◽  
pp. 878-882 ◽  
Author(s):  
Lars Jørgensen ◽  
Steven J. McKerrall ◽  
Christian A. Kuttruff ◽  
Felix Ungeheuer ◽  
Jakob Felding ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Anticancer Activity ◽  
Actinic Keratosis ◽  
Skin Condition ◽  
Chemical Production ◽  
Two Phase ◽  
Chemical Complexity ◽  
Euphorbia Peplus ◽  
Stereocontrolled Synthesis ◽  
Phase Design

Ingenol is a diterpenoid with unique architecture and has derivatives possessing important anticancer activity, including the recently Food and Drug Administration–approved Picato, a first-in-class drug for the treatment of the precancerous skin condition actinic keratosis. Currently, that compound is sourced inefficiently from Euphorbia peplus. Here, we detail an efficient, highly stereocontrolled synthesis of (+)-ingenol proceeding in only 14 steps from inexpensive (+)-3-carene and using a two-phase design. This synthesis will allow for the creation of fully synthetic analogs of bioactive ingenanes to address pharmacological limitations and provides a strategic blueprint for chemical production. These results validate two-phase terpene total synthesis as not only an academic curiosity but also a viable alternative to isolation or bioengineering for the efficient preparation of polyoxygenated terpenoids at the limits of chemical complexity.

scholarly journals Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins Allowing a Formal Synthesis of Trichoderone A

2021 ◽  
Author(s):  
Oscar Gayraud ◽  
Benjamin Laroche ◽  
Nicolas Casaretto ◽  
Bastien Nay
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Two Phase ◽  
Formal Synthesis ◽  
Diels Alder Reaction ◽  
Oxidative Transformations ◽  
High Degree

Aspochalasins are leucine-derived cytochalasins. Their complexity is often associated to a high degree of biosynthetic oxidative transformations that could inspire a two-phase strategy in total synthesis. In that context, we describe the synthesis of a putative biomimetic tetracyclic intermediate. The key constructive steps are an intramolecular Diels-Alder reaction to install the characteristic isoindolone core of cytochalasins, whose branched precursor was obtained from a stereoselective Ireland-Claisen rearrangement made on a highly unsaturated substrate. This work also constitutes a formal synthesis of trichoderone A.

scholarly journals Synthesis of a Biomimetic Tetracyclic Precursor of Aspochalasins Allowing a Formal Synthesis of Trichoderone A

2021 ◽  
Author(s):  
Oscar Gayraud ◽  
Benjamin Laroche ◽  
Nicolas Casaretto ◽  
Bastien Nay
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Two Phase ◽  
Formal Synthesis ◽  
Diels Alder Reaction ◽  
Oxidative Transformations ◽  
High Degree

Aspochalasins are leucine-derived cytochalasins. Their complexity is often associated to a high degree of biosynthetic oxidative transformations that could inspire a two-phase strategy in total synthesis. In that context, we describe the synthesis of a putative biomimetic tetracyclic intermediate. The key constructive steps are an intramolecular Diels-Alder reaction to install the characteristic isoindolone core of cytochalasins, whose branched precursor was obtained from a stereoselective Ireland-Claisen rearrangement made on a highly unsaturated substrate. This work also constitutes a formal synthesis of trichoderone A.

Two-Phase Synthesis of Taxol®

2020 ◽  
Author(s):  
Yuzuru Kanda ◽  
Hugh Nakamura ◽  
Shigenobu Umemiya ◽  
Ravi Kumar Puthukanoori ◽  
Venkata Ramana Murthy Appala ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Anticancer Agent ◽  
Synthetic Approach ◽  
Two Phase ◽  
Phase Synthesis ◽  
Natural Plant ◽  
Natural Isolates ◽  
Terpene Synthesis ◽  
The Subject ◽  
Biosynthetic Machinery

<p>Taxol® is widely regarded as amongst the most famed natural isolates ever discovered, and has been the subject of innumerable studies in both basic and applied science. Its documented success as an anticancer agent, coupled with early concerns over supply, stimulated a furious worldwide effort from chemists to provide a solution for its preparation through total synthesis. Those pioneering studies proved the feasibility of retrosynthetically-guided access to synthetic Taxol, albeit in minute quantities and with enormous effort. In practice, all medicinal chemistry efforts and eventual commercialization have relied upon natural- (plant</p> <p>material) or biosynthetically-derived (synthetic biology) supplies. Here we show how a complementary divergent synthetic approach that is holistically patterned off of biosynthetic machinery for terpene synthesis can be used to arrive at Taxol®.</p>

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