Synthesis of 3‐Oxaterpenoids and Its Application in the Total Synthesis of (±)‐Moluccanic Acid Methyl Ester

Li, Bin; Lai, Yin-Chang; Zhao, Yujun; Yiu‐hang, Wong,; Shen, Zhi‐Liang; Loh, Teck‐Peng

doi:10.1002/ange.201205981

Cited by 20 publications

(2 citation statements)

References 72 publications

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“…[53] This reaction proceeded through the quenching of the intermediate tetrahydropyranyl cation through an intramolecular Friedel-Crafts reaction. [53] This reaction proceeded through the quenching of the intermediate tetrahydropyranyl cation through an intramolecular Friedel-Crafts reaction.…”

Section: Prins-type Cyclizations As Entries To Other Systemsmentioning

confidence: 99%

Prins‐Type Cyclization Reactions in Natural Product Synthesis

2013

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Prins‐type cyclization reactions proceed through the intramolecular addition of a π‐nucleophile to an oxocarbenium ion or related species to generate a ring through carbon–carbon bond formation, often with excellent and predictable stereocontrol. The widespread presence of naturally occurring oxygen‐containing heterocycles has made these reactions exceedingly valuable for total synthesis efforts. This microreview covers several common variations of Prins‐type cyclizations and highlights their applicability to the total synthesis of natural products and analogs.

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Section: Prins-type Cyclizations As Entries To Other Systemsmentioning

confidence: 99%

Prins‐Type Cyclization Reactions in Natural Product Synthesis

2013

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“…An InBr 3 -catalyzed Prins and Friedel-Crafts cyclizations have also shown to afford polycyclic ring compounds. 11 This methodology was utilized in the synthesis of moluccanic acid methyl ester.…”

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confidence: 99%

FeCl3-catalyzed tandem Prins and Friedel–Crafts cyclization: a highly diastereoselective route to polycyclic ring structures

Ghosh

Keyes

Veitschegger

2014

Tetrahedron Letters

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Catalytic FeCl3 in the presence of 4Å molecular sieves has been shown to effect highly diastereoselective tandem Prins and Friedel-Crafts cyclization of substituted (E/Z)-6-phenylhex-3-en-1-ol and a variety of aldehydes to provide a range of polycyclic compounds in good to excellent yields. The reaction of an enantioenriched alcohol with an aldehyde provided the cyclization product without loss of optical activity. Furthermore, a Lewis acid catalyzed ring opening resulted in functionalized tetralin derivatives with multiple chiral centers.

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Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

Maji

2019

Adv Synth Catal

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Ther eview is aimeda tdescribingt he advances in electrophilic "iranium" ion-triggered Friedel-Crafts-type alkylation for polyenec yclizations. Owing to the greatp otential of halo-, seleno-and sulfeno-functionalized Friedel-Crafts alkylated compounds,n umerous catalytic methodsh aveb een developed in either racemico re nantiopure forms. More importantly,t hese arene-alkylated or polyenecyclized productsc ontaining halo,s eleno ands ulfeno functionality couldb eu seful in further synthetic planning to access biologically active molecules and natural productsw ith highly complex architectures. Starting from aw ide range of classicalL ewis acids, Brønsted acids and Lewis bases through to the very recently developed halogen bondc atalysts (XB-cat.), selenonium cations as Lewis acids etc. are utilized to access these types of compounds.M orer ecently, some of the co-operative catalytic systems such as phosphite-thiourea, sulfonic acid-phosphoramidite, sulfonic acid-selenophosphoramide,s ulfonic acidanion binding thiourea, etc. catalyzing highly diastereo-and enantioselective polyene cyclizations have also been described. Thec onfigurational stability,r eactivity and selectivity of three-membered cationic

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Synthesis of 3‐Oxaterpenoids and Its Application in the Total Synthesis of (±)‐Moluccanic Acid Methyl Ester

Cited by 20 publications

References 72 publications

Prins‐Type Cyclization Reactions in Natural Product Synthesis

Prins‐Type Cyclization Reactions in Natural Product Synthesis

FeCl3-catalyzed tandem Prins and Friedel–Crafts cyclization: a highly diastereoselective route to polycyclic ring structures

Stereoselective Haliranium, Thiiranium and Seleniranium Ion‐Triggered Friedel–Crafts‐Type Alkylations for Polyene Cyclizations

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