Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent

Wei Jan Huang, Om V. Singh, Chung Hsiung Chen, Shoei Sheng Lee

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Condensation of 3,4-dimethoxybenzeneethanamine (3d) and various benzeneacetic acids, i.e., 4a-e, via a practical and efficient one-pot Bischler-Napieralski reaction, followed by NaBH4 reduction, produced a series of 1-benzyl-1,2,3,4-tetrahydroisoquinolines, i.e., 5a-e, in satisfactory yields (Scheme 3). Oxidative coupling of the N-acyl and N-methyl derivatives 6a-e of the latter with hypervalent iodine ([IPh(CF 3COO)2]) yielded products with two different skeletons (Scheme 4). The major products from N-acyl derivatives 6a-c were (±)-N-acylneospirodienones 2a-c, while the minor was the 3,4-dihydroisoquinoline 7. (±)-Glaucine (1), however, was the major product starting from N-methyl derivative 6e. Possible reaction mechanisms for the formation of these two types of skeleton are proposed (Scheme 5).

Original languageEnglish
Pages (from-to)167-174
Number of pages8
JournalHelvetica Chimica Acta
Volume87
Issue number1
DOIs
Publication statusPublished - 2004
Externally publishedYes

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Oxidative Coupling
Iodine
Skeleton
iodine
reagents
Phenylacetates
Derivatives
musculoskeletal system
synthesis
products
Condensation
condensation
acids
Acids
glaucine
G 1616
1,2,3,4-tetrahydro-1-(phenylmethyl)isoquinoline

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of (±)-Glaucine and (±)-Neospirodienone via an One-Pot Bischler-Napieralski Reaction and Oxidative Coupling by a Hypervalent Iodine Reagent. / Huang, Wei Jan; Singh, Om V.; Chen, Chung Hsiung; Lee, Shoei Sheng.

In: Helvetica Chimica Acta, Vol. 87, No. 1, 2004, p. 167-174.

Research output: Contribution to journalArticle

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AU - Singh, Om V.

AU - Chen, Chung Hsiung

AU - Lee, Shoei Sheng

PY - 2004

Y1 - 2004

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