Base-Dependent Divergent Annulation of 4-Chloro-3-formylcoumarin and Tetrahydroisoquinoline: Application to the Synthesis of Isolamellarins and Hydroxypyrrolones
A series of pyrrolo[2,1-a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G...
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| Vydané v: | Journal of organic chemistry Ročník 84; číslo 6; s. 3662 - 3670 |
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| Hlavní autori: | , |
| Médium: | Journal Article |
| Jazyk: | English |
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WASHINGTON
Amer Chemical Soc
15.03.2019
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| Abstract | A series of pyrrolo[2,1-a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G trimethyl ether). When exposed to UV light, the pyrrolo[2,1-a]isoquinoline- and coumarin-fused pentacycles B were found to undergo aerobic oxidation to give the corresponding hydroxypyrrolones. |
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| AbstractList | A series of pyrrolo[2,1- a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G trimethyl ether). When exposed to UV light, the pyrrolo[2,1- a]isoquinoline- and coumarin-fused pentacycles B were found to undergo aerobic oxidation to give the corresponding hydroxypyrrolones. A series of pyrrolo[2,1- a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G trimethyl ether). When exposed to UV light, the pyrrolo[2,1- a]isoquinoline- and coumarin-fused pentacycles B were found to undergo aerobic oxidation to give the corresponding hydroxypyrrolones.A series of pyrrolo[2,1- a]isoquinoline and coumarin-fused pentacyclic derivatives were synthesized via base-mediated divergent annulation of 4-chloro-3-formylcoumarin and tetrahydroisoquinoline as a key step. This method was then extended to the preparation of isolamellarins A and B (isolamellarin G trimethyl ether). When exposed to UV light, the pyrrolo[2,1- a]isoquinoline- and coumarin-fused pentacycles B were found to undergo aerobic oxidation to give the corresponding hydroxypyrrolones. |
| Author | Yang, Ding-Yah Vyasamudri, Sameer |
| Author_xml | – sequence: 1 givenname: Sameer surname: Vyasamudri fullname: Vyasamudri, Sameer organization: Tunghai Univ, Dept Chem, 1727,Sec 4,Taiwan Blvd, Taichung 40704, Taiwan – sequence: 2 givenname: Ding-Yah orcidid: 0000-0002-3611-2042 surname: Yang fullname: Yang, Ding-Yah email: yang@thu.edu.tw organization: Tunghai Univ, Dept Chem, 1727,Sec 4,Taiwan Blvd, Taichung 40704, Taiwan |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30807162$$D View this record in MEDLINE/PubMed |
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| Keywords | LAMELLARIN-ALPHA 20-SULFATE CHILENINE INHIBITORS DERIVATIVES ALKALOIDS |
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| Title | Base-Dependent Divergent Annulation of 4-Chloro-3-formylcoumarin and Tetrahydroisoquinoline: Application to the Synthesis of Isolamellarins and Hydroxypyrrolones |
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