Author
Sylvain Collet
Bio: Sylvain Collet is an academic researcher from University of Nantes. The author has contributed to research in topics: Chiral auxiliary & Carbocation. The author has an hindex of 5, co-authored 11 publications receiving 125 citations.
Papers
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TL;DR: A convergent synthesis of the naturally occurring alkaloid Calothrixin B is presented, which used a regioselective hetero-Diels-Alder reaction between a "push-pull" 2-aza-diene and a N-protected 3-bromo-9H-carbazole-1,4-dione to construct the five-ring skeleton of the molecule.
Abstract: A convergent synthesis of the naturally occurring alkaloid Calothrixin B is presented, which used a regioselective hetero-Diels−Alder reaction between a “push−pull” 2-aza-diene and a N-protected 3-...
61 citations
TL;DR: The cycloaddition of 2- or 2,3-substituted 1-thia- and 1 -thia-3-aza-4-dimethylamino-buta-1, 3-dienes with various dienophiles in the presence of a Lewis acid provides a rapid and diastereoselective access to the 3,4-dihydro-2H-thiopyran and 5,6-diphysine backbones as discussed by the authors.
21 citations
TL;DR: In this article, an investigation of the one-carbon homologation of some 1-tribromomethyl-isoquinoline derivatives was conducted, and a mechanism for ring enlargement involving initial formation of an aziridinium, and its subsequent opening to form a stabilized benzylic carbocation, was proposed to explain the results.
17 citations
TL;DR: In this article, a twelve-step synthesis of ( −)-(R)-sumanirole starting from quinoline is described, using a chiral Reissert adduct.
16 citations
TL;DR: In this article, a short and efficient synthesis of calothrixin B is reported, where the key reaction is a hetero-Diels-Alder reaction between 3-bromo-9H-carbazole-1,4-dione and a 'push-pull' 2-aza-1-3-diene.
Abstract: A new short and efficient synthesis of calothrixin B is reported. The key reaction is a hetero-Diels-Alder reaction between 3-bromo-9H-carbazole-1,4-dione and a 'push-pull' 2-aza-1,3-diene.
7 citations
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947 citations
TL;DR: This overview should allow chemists to gain insight into the factors governing the regioselectivity in aziridinium ring openings and inherent structural features such as the nature of the C2 aziridine substituent and the natureof the electrophile and the nucleophile.
Abstract: In this critical review, the ring opening of non-activated 2-substituted aziridinesvia intermediate aziridinium salts will be dealt with. Emphasis will be put on the relationship between the observed regioselectivity and inherent structural features such as the nature of the C2 aziridine substituent and the nature of the electrophile and the nucleophile. This overview should allow chemists to gain insight into the factors governing the regioselectivity in aziridinium ring openings (81 references).
360 citations
TL;DR: This Review summarizes the progress achieved in the chemistry of tetrahydroquinolines, with emphasis on their synthesis, during the period from mid-2010 to early 2018.
Abstract: Tetrahydroquinoline is one of the most important simple nitrogen heterocycles, being widespread in nature and present in a broad variety of pharmacologically active compounds. This Review summarizes the progress achieved in the chemistry of tetrahydroquinolines, with emphasis on their synthesis, during the period from mid-2010 to early 2018.
231 citations
TL;DR: These compounds are found in natural products and antibiotics, and are also considered important precursors for pharmacologically interesting β-lactams and other bioactive compounds.
Abstract: In consequence of their biological e
ff
ects, conformationally
constrained carbocyclic
β
-amino acids have generated great
interest among synthetic and medicinal chemists in the past 2
decades, and they have become a hot topic in organic and
bioorganic chemistry. These compounds are found in natural
products and antibiotics. They are also considered important
precursors for pharmacologically interesting
β
-lactams and
other bioactive compounds. Certain carbocyclic
β
-amino acids,
e.g., cispentacin , icofungipen , and BAY Y9379 ,
possess noteworthy antifungal or antibacterial activities, while
tilidin , a phenyl-substituted cyclohexene amino ester, is an
analgetic.
151 citations
TL;DR: The development of asymmetric, in particular catalytic enantioselective intramolecular aza-Diels-Alder reaction in the total synthesis of natural products remains highly challenging, and will no doubt see enormous advances in the future.
Abstract: The Diels-Alder reaction that involves a nitrogen atom in the diene or dienophile is termed the aza-Diels-Alder reaction. As well as the powerful all-carbon Diels-Alder reaction, the aza-Diels-Alder reaction has also played an important role in the total synthesis of natural products. Herein, we review various natural products using an aza-Diels-Alder reaction as a key step to their total synthesis, and divide the syntheses into inter- and intra-molecular aza-Diels-Alder reactions and a retro-aza-Diels-Alder reaction. Inter- and intra-molecular aza-Diels-Alder reactions involve an imine as an electron deficient dienophile and an imine as an electron deficient azadiene. The significance of the aza-Diels-Alder reaction for the construction of a six-membered ring containing nitrogen is tremendous, but the development of asymmetric, in particular catalytic enantioselective intramolecular aza-Diels-Alder reaction in the total synthesis of natural products remains highly challenging, and will no doubt see enormous advances in the future.
84 citations