Studies on the Components of &lt;i&gt;Aristolochia debilis&lt;/i&gt;. I

Kariyone, Tatsuo; Naito, Seiji

doi:10.1248/yakushi1947.75.12_1511

Cited by 14 publications

(10 citation statements)

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“…We also prepared 1,6‐enyne 126 from triflate 129 (Scheme ) . Unfortunately, in contrast to that found in the reaction of 1‐ethynyl‐2‐allylbenzene, which gives the 6‐membered ring ketone by a 6‐ endo ‐ dig process, the gold(I)‐catalyzed oxidative reaction of 126 proceeded exclusively by the 6‐ exo ‐ dig mode to form 131 .…”

Section: Diastereoselective Cyclizations Of 15‐enynesmentioning

confidence: 76%

“…We also used a gold(I)‐catalyzed cycloisomerization of a 1,5‐enyne for the synthesis of nardoaristolone B ( 122 ), isolated the plant Nardostachys chinensis batal, endemic of the Himalayan mountains . The related sesquiterpene (−)‐aristolone ( 123 ) was isolated from the roots of Aristochia debilis …”

Section: Diastereoselective Cyclizations Of 15‐enynesmentioning

confidence: 99%

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Gold(I)‐Catalysis for the Synthesis of Terpenoids: From Intramolecular Cascades to Intermolecular Cycloadditions

Mayans

Armengol-Relats

Calleja

et al. 2018

Israel Journal of Chemistry

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Gold(I)‐catalyzed cycloisomerizations of 1,n‐enynes proceed through electrophilic intermediates that can be trapped intra‐ or intermolecularly by a variety of hetero‐ and carbon nucleophiles to form complex skeletons in a single step. This review covers the efforts of our group towards the development of new reactions that have been successfully applied in the total synthesis of several natural terpenoids and related carbocyclic structures, as well as for the ready access to challenging linear acenes.

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Section: Diastereoselective Cyclizations Of 15‐enynesmentioning

confidence: 76%

Section: Diastereoselective Cyclizations Of 15‐enynesmentioning

confidence: 99%

Gold(I)‐Catalysis for the Synthesis of Terpenoids: From Intramolecular Cascades to Intermolecular Cycloadditions

Mayans

Armengol-Relats

Calleja

et al. 2018

Israel Journal of Chemistry

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“…In fact, in our hands, compound 1 in recemic form showed excellent mosquito‐repellent activity against the Aedes mosquito, which is the vector for Dengue fever and the Zika virus . Isolation of the closely related sesquiterpene (–)‐Aristolone ( 6 ) was reported in 1955 from the roots of Aristochia debilis , and its several syntheses were reported in the literature . There are a few more natural products reported in the literature like Lindenene ( 2 ) and Chloranthalactone A ( 3 ), having a similar 3/5/6 structural core as Nardoaristolone B (Figure ).…”

Section: Introductionmentioning

confidence: 99%

A Total Synthesis of (–)‐Nardoaristolone B

et al. 2016

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A stereoselective total synthesis of (–)‐Nardoaristolone B, a nor‐aristolane sesquiterpenoid natural product with an unusual 3/5/6 tricyclic ring system is described. The highlights of the present work includes use of (+)‐(R)‐Pulegone as a chiral‐pool starting material, ring‐closing metathesis, allylic oxidation and stereoselective cyclopropanation. In addition, a new analogue of Nardoaristolone B (minor product from the final step) was isolated in pure form and fully characterized with the help of single‐crystal X‐ray analysis.

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“…The sesquiterpene aristolene was first isolated by Kariyone & Naito (1955) from Aristolchia debilis Sieb. et Zucc.…”

Section: Introductionmentioning

confidence: 99%