Diastereoselective oxygen to carbon rearrangements of anomerically linked enol ethers and the total synthesis of (+)-(S,S )-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a component of civet

Dixon, Darren J.; Ley, Steven V.; Tate, Edward W.

doi:10.1039/b001243m

Cited by 59 publications

(28 citation statements)

References 37 publications

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“…The second portion of the substrate was synthesized starting with TBS protection and ozonolysis of known alcohol 13 16 to obtain 14 in 95% yield over two steps (Scheme 2). Takai olefination 17 with a CrCl 2 /CHI 3 combination followed by TBS removal gave alcohol 15 in 64% yield.…”

Section: Resultsmentioning

confidence: 99%

Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities

et al. 2011

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Cysteine plays a number of important functional and structural roles in Nature, often in the realm of catalysis. Herein, we present an example of a cysteine-catalyzed Rauhut-Currier reaction for a potentially biomimetic synthesis of Sch-642305 and related analogs. In this key step of the synthesis we discuss interesting new discoveries and the importance of substrate-catalyst recognition, as well as cysteine’s structural features. Also, we investigate the activity of Sch-642305 and four analogs in HIV-infected T-cells.

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Section: Resultsmentioning

confidence: 99%

Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities

et al. 2011

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“…Compound 4 [11] (342 mg, 3 mmol) and catalyst Ru-II (100 mg, 0.12 mmol) were dissolved under N 2 in dry, deoxygenated CH 2 Cl 2 (20 mL). The mixture was then heated at reflux.…”

Section: -[(2s3s6r)-3-(benzyloxy)-6-[(s)-6-hydroxyhept-1ez-enyl]tmentioning

confidence: 99%

Synthesis and Biological Properties of the Cytotoxic 14‐Membered Macrolides Aspergillide A and B

Díaz‐Oltra

Murga

Falomir

et al. 2010

Chemistry A European J

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“…[13,14] Thus, alkenes 8 and 9 were prepared by copper-catalyzed acylation and alkylation of the corresponding Grignard reagents, respectively. [15,16] Using our one-pot homologation the corresponding (E)-a,b-unsaturated acids 9-ODA and 9-HDA were obtained in good yields and perfect selectivity. To the best of our knowledge these are the shortest synthesis of these two honey bee pheromones which are completely free of protecting groups.…”

mentioning

confidence: 98%

Practical Synthesis of (E)‐α,β‐Unsaturated Carboxylic Acids Using a One‐Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence

2008

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Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, onepot procedure for the synthesis of (E)-a,b-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-a,b-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA [(E)-9-oxodec-2-enoic acid] and 9-HDA [(E)-9-hydroxydec-2-enoic acid].

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Diastereoselective oxygen to carbon rearrangements of anomerically linked enol ethers and the total synthesis of (+)-(S,S )-(cis-6-methyltetrahydropyran-2-yl)acetic acid, a component of civet

Cited by 59 publications

References 37 publications

Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities

Quasi-biomimetic ring contraction promoted by a cysteine-based nucleophile: Total synthesis of Sch-642305, some analogs and their putative anti-HIV activities

Synthesis and Biological Properties of the Cytotoxic 14‐Membered Macrolides Aspergillide A and B

Practical Synthesis of (E)‐α,β‐Unsaturated Carboxylic Acids Using a One‐Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence

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