Facile generation and trapping of. alpha.-oxo-o-quinodimethanes: synthesis of 3-aryl-3, 4-dihydroisocoumarins and protoberberines

SV Kessar, P Singh, R Vohra, NP Kaur…

Index: Kessar; Singh; Vohra; Kaur; Venugopal Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6716 - 6720

Full Text: HTML

Citation Number: 28

Abstract

Fluorodesilylation of o-((trimethyleily1) methyl) benzoyl derivatives 5 in the presence of aromatic aldehydes and alkyl fumarates gives 3-aryl-3, 4-dhydro~ oumarina 6 and a- tetralones 10, respectively. Reaction of 5 with 3, 4-dihydroieoquinolinium salts 19 leads to 8- oxoberbines 21. Using this procedure, racemic hydrangenol, phyllodulcin, tetrahydropalmatine (224, and canadine (22b) have been synthesized.

Related Articles:

A regiospecific synthesis of protoberberine alkaloids

[Kiparissides, Zinovia; Fichtner, Robert H.; Poplawski, Janusz; Nalliah, Bala C.; MacLean, David B. Canadian Journal of Chemistry, 1980 , vol. 58, p. 2770 - 2779]

A regiospecific synthesis of protoberberine alkaloids

[Kiparissides, Zinovia; Fichtner, Robert H.; Poplawski, Janusz; Nalliah, Bala C.; MacLean, David B. Canadian Journal of Chemistry, 1980 , vol. 58, p. 2770 - 2779]

A review on medicinal plants exhibiting antifertility activity in males

[Bhakuni, D. S.; Kumar, Praveen Journal of the Indian Chemical Society, 1988 , vol. 65, p. 417 - 421]

Convenient synthesis of 2, 3, 9, 10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids.

[Hanaoka, Miyoji; Hirasawa, Taeko; Cho, Won Jea; Yasuda, Shingo Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 3 p. 399 - 404]

A new and convenient synthesis of protoberberine alkaloids:(±)-tetrahydropalmatine,(±)-sinactine,(±)-canadine, and (+)-stylopine

[Yasuda, Shingo; Hirasawa, Taeko; Hanaoka, Miyoji Tetrahedron Letters, 1987 , vol. 28, # 21 p. 2399 - 2402]

More Articles...