Observations regarding eschenmoser sulfide contractions of β-oxygenated thiolactams

Hart, David S.; Sun, Li Qiang; Kozikowski, Alan P.

doi:10.1016/0040-4039(95)01648-2

Cited by 16 publications

(12 citation statements)

References 17 publications

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“…Several possibilities were considered for converting the oxazole imide 13 to the desired acetylenic oxazole 16 . However, by far the most convenient procedure made use of the methoxylactam 15 , which was readily derived from 13 by selective reduction with NaBH 4 , followed by treatment with MeOH/H + . Finally, BF 3 ·Et 2 O catalyzed condensation of 15 with (1-propynyl)tributylstannane gave a 92% yield of the target oxazole 16 …”

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confidence: 99%

Total Synthesis of (±)-Stemoamide

Jacobi

Lee

1997

J. Am. Chem. Soc.

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confidence: 99%

Total Synthesis of (±)-Stemoamide

Jacobi

Lee

1997

J. Am. Chem. Soc.

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“…Recently, Hart and co-workers have reported a Lewis acid mediated allylation reaction from a related pyrrolidine (Scheme 7). 12 They showed that the cis-isomer was the major product in this reaction probably due to the directing effect of the tert-(butyldimethylsilyl)oxy (OTBS) group.…”

Section: Scheme 6 Synthesis Of Pyrrolidine 1 a A Prepared By Colleagumentioning

confidence: 99%

“…According to Hart's procedure, introduction of the allyl side chain was achieved using allyl trimethylsilane in the presence of titanium tetrachloride to afford 5 (Scheme 8). 12 The Boc protecting group was unexpectedly removed during the course of the reaction prior to purification. 13 In addition, the product mixture proved to be sensitive to purification by chromatography on silica gel.…”

Section: Scheme 7 Lewis Acid Mediated Allylationmentioning

confidence: 99%

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Three Essays on Applied Semiparametric Methods

Zhang¹

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Total synthesis of ht-13-A and ht-13-B, total synthesis of aurantioclavine, progress towards the synthesis of cycloclavine. Yilin Zhang Total synthesis of tetracyclic indole alkaloid ht-13-A and ht-13-B has been accomplished from commercially available (S)-4-amino-2-hydroxybutyric acid and trans-4-hydroxy-L-proline respectively. The key synthetic steps include an acyliminium ion allylation, a Mitsunobu reaction, a palladium-catalyzed Stille-Kelly cross coupling reaction, and a carbon monoxide mediated palladium-catalyzed reductive Nheterocyclization. The total synthesis of aurantioclavine has been studied. The synthesis commenced with 2-amino-3-nitrophenol. Key synthetic steps include a Stille coupling reaction, a Heck reaction, a Lewis acid mediated cyclization and a carbon monoxide mediated palladium-catalyzed reductive N-heterocyclization. In addition, the first asymmetric total synthesis of (+)-cycloclavine has been studied. Key synthetic steps include a ring closing metathesis, an acyliminium ion allylation and a Stille coupling. iii Dedicated to my Parents, Kun Zhang and Yuling Sun First and foremost, I would like to thank my research advisor, Dr. Björn Söderberg, for all of his support for me to complete Ph.D. With his patience, I have learned organic chemistry and organic laboratory skills. In addition, I am very grateful to his guidance through all the difficulties I encountered during my research work. Furthermore, I sincerely appreciate the members of my committee, Drs. Kung Wang, John Penn, Glen Jackson, and Yon Rojanasakul for their valuable involvement throughout my entire graduate study. I appreciate the assistance and friendship of my co-workers in the Söderberg group,

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“…Reasons for the different approaches include the failure of the ring to react under Mitsunobu reaction, failure to react to form the correct ring, and lack of literature precedence to form the correct stereoisomer. The original method used for the construction of the pyrrolidine ring was following a literature procedure102 , although forming the enantiomer of the publisher sequence (Scheme 14). The synthesis starts from commercially available (R)-malic acid reacting with acetyl chloride and methylamine to form the imide 49.…”

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Synthesis of substituted 2-vinyl and 2-phenylbenzimidazoles and progress towards the synthesis of natural products ht-13-A and ht-13-B

Hubbard¹

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Synthesis of 2-alkenyl and 2-arylbenzimidazoles, having a variety of functional groups, has been accomplished via a novel palladium-catalyzed reductive N-heteroannulation of 2-nitro-N-alkyl or N-benzyl benzenamines. The cyclization precursors are readily prepared from commercially available compounds by a variety of methods. In addition, the first total synthesis of ht-13-A has been studied. The key steps of the synthesis are a Mitsunobu reaction, an intramolecular Heck reaction, and a reductive Nheteroannulation.

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Observations regarding eschenmoser sulfide contractions of β-oxygenated thiolactams

Cited by 16 publications

References 17 publications

Total Synthesis of (±)-Stemoamide

Total Synthesis of (±)-Stemoamide

Three Essays on Applied Semiparametric Methods

Synthesis of substituted 2-vinyl and 2-phenylbenzimidazoles and progress towards the synthesis of natural products ht-13-A and ht-13-B

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