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Recent applications in natural product synthesis of dihydrofuran and -pyran formation by ring-closing alkene metathesis.
- Reece Jacques, R. Pal, +4 authors D. M. Hodgson
- Chemistry, Medicine
- Organic & biomolecular chemistry
- 22 June 2016
In the past two decades, alkene metathesis has risen in prominence to become a significant synthetic strategy for alkene formation. Many total syntheses of natural products have used this… Expand
Total Synthesis of (S)-(-)-Curvularin: A Ring-Closing-Metathesis-Based Constructionof the Macrocyclic Framework
A convergent, flexible, and efficient approach to the synthesis of curvularin is described. Key step is the high-yielding macrocyclic ring formation by ring-closing metathesis (RCM) using the Grubbs… Expand
Stereoselective synthesis of the densely functionalized C1-C9 fragment of amphidinolides C and F
The synthesis of the C1–C9 subunit of amphidinolides C and F is described. Key steps include tandem Sharpless asymmetric dihydroxylation-SN2 cyclization reaction, Lewis acid-mediated epoxide opening,… Expand
Anionic [4 + 2] cycloaddition with thiophthalides: an integrated approach to the synthesis of olivin and pillaromycinone
A systematic study of the potential reactivity of the thiophthalides 4 and 18–20 as 1,4-dipolar synthons, has shown that 3-phenylthiothiophthalide 19 is the best annulating agent for the preparation… Expand
Stereospecific formation of 2-[(E)-alk-1′-enyl]benzoic acids in an unusual reaction of thiophthalides with aldehydes
The reaction of thiophthalides 1 with aldehydes 3 in the presence of lithium tert-butoxide at –60 to 25 °C results in the stereospecific formation of only trans 2-(alk-1′-enyl)benzoic acids 4 in… Expand
STEREOSELECTIVE FORMAL TOTAL SYNTHESIS OF NOVEL ANTIBIOTIC (-)-CENTROLOBINE
A concise and stereoselective formal total synthesis of (-)-centrolobine is achieved utilizing Mioskowski's Lewis acid mediated epoxide opening followed by ring-closing metathesis as the key reaction.
Direct glycosylation with anomeric hydroxy sugars by activation with 3-fluorophthalic anhydride and trifluoromethanesulfonic anhydride
An efficient and direct one-pot glycosylation method using anomeric hydroxy sugars as glycosyl donors, employing 3-fluorophthalic anhydride and triflic anhydride as activating agents, has been… Expand
A Convenient Synthesis of Aromatic Thiolactones
Abstract Hydrolytic decomposition of thiouronium salts A with aqueous NaHCO3 at 80° – 90 °C directly furnished thiolactones 6 -10 in very good yields in one-flask operation.
Radical halogenation-mediated latent-active glycosylations of allyl glycosides.
Radical halogenation-mediated glycosylation using allyl glycosides as donors and as acceptors emerges to be an efficient and hither-to unknown glycosylation method, adhering to the concept of the… Expand
Hauser annulation of furoindolones in the synthesis of carbazole-1,4-quinones and benzo[b]carbazoloquinones
N-Boc/MOM-protected furoindolones, synthesized in four steps, have been successfully employed in the Hauser annulations with Michael acceptors to provide a new synthesis of carbazole-1,4-quinones.… Expand