Total Synthesis of (–)‐Isopisiferin: Confirmation of Absolute Configuration

Jan, Ning‐Wei; Liu, Hsing‐Jang; Hsieh, Min‐Tsang; Shia, Kak‐Shan

doi:10.1002/ejoc.201000449

Cited by 8 publications

(3 citation statements)

References 16 publications

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“…Treament of 11 with a catalytic amount of p TsOH in refluxing benzene directly gave the desired tricyclic compound 12 in 96% yield. By deprotection with EtSNa, 12 was easily converted into the target molecule 1b in 94% yield. Initial attempts to deprotect the methyl ether by using BBr 3 were unsuccessful, and only a complex mixture was obtained.…”

Section: Resultsmentioning

confidence: 99%

Total Syntheses of Cladoacetals A and B: Confirmation of Absolute Configurations

Hsu

Lin

2012

J. Org. Chem.

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The first enantioselective syntheses of cladoacetals A (1a, overall yield: 16%) and B (1b, overall yield: 34%) from crotonaldehyde in nine and seven steps, respectively, have been accomplished. Sharpless asymmetric dihydroxylation, Suzuki coupling, and acid-catalyzed intramolecular acetalization were the key steps in the syntheses. The absolute configuration of natural (+)-cladoacetal A was affirmed to be 1S,3S,4R, whereas that of (-)-cladoacetal B was affirmed to be 1R,3S,4S.

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Section: Resultsmentioning

confidence: 99%

Total Syntheses of Cladoacetals A and B: Confirmation of Absolute Configurations

Hsu

Lin

2012

J. Org. Chem.

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“…[82] In 2010, Shia and coworkers reported an asymmetric approach to (À )-isopisiferin (150) that served to confirm the absolute configuration of the natural product (Scheme 11). [83] Starting from the optically enriched aldehyde 143, a 1,2-addition of the aryl lithium derived from the aryl bromide 144 and subsequent acid-mediated elimination of the resultant alcohol afforded the styrene 145 in 75 % over two steps. Conversion of the vinyl iodide moiety to a carboxylic acid and removal of the styrene unsaturation to give 146 was achieved in three steps in 85 % overall yield, which set the stage for the key ringclosing event.…”

Section: Highlighted Recent Synthetic Efforts Toward Icetexanesmentioning

confidence: 99%

Recent Developments with Icetexane Natural Products

Chain

Naeini

Ziegelmeier

2022

Chemistry & Biodiversity

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Icetexane diterpenoids are a diverse family of natural products sourced from several species of terrestrial plants. Icetexanes exhibit a broad array of biological activities and together with their complex 6‐7‐6 tricyclic scaffolds, they have piqued the interest of synthetic organic chemists, natural products chemists, and biological investigators over the past four decades and were reviewed 13 years ago. This review summarizes icetexane natural products isolated since 2009, provides an overview of new synthetic approaches to the icetexane problem, and proposes an additional classification of icetexanes based on novel structures that are unlike previously isolated materials.

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“…12,[163][164][165][166][167][168][169] The [6,7,6]-icetexane skeleton has also attracted synthetic interest. 13,[170][171][172] Further examples of diterpenoids with this skeleton include the ortho-quinone przewalskin E 49 from Salvia przewalskii, 173 whilst icetexane I is a related ocatechol that was obtained 174 from Premna tomentosa (Verbenaceae). The trigonostemons are noricetexanes lacking C-16 and C-17, which were isolated 175 from Trigonostemon chinensis (Euphorbiaceae).…”

Section: Tricyclic Diterpenoids 41 Abietanesmentioning

confidence: 99%