Issue 27, 2012
From the journal:

Organic & Biomolecular Chemistry

Asymmetric formal synthesis of schulzeines A and C†

Jaebong Jang,a   Jong-Wha Jung,b   Jaeseung Ahn,a   Jaehoon Sim,a   Dong-Jo Chang,a   Dae-Duk Kima  and  Young-Ger Suh*a  

* Corresponding authors

a College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 151-742, Korea
E-mail: ygsuh@snu.ac.kr
Fax: +82-2-888-0649
Tel: +82-2-880-7875

b College of Pharmacy, Kyungpook National University, Daegu 702-701, Korea

Abstract

The asymmetric formal synthesis of schulzeines A and C is described. Key features of the synthesis include the efficient and stereoselective construction of the benzoquinolizidine skeleton via the aza-Claisen rearrangement-induced ring expansion of the 1-vinyl-N-glycyl-isoquinoline, which was prepared by the highly enantioselective asymmetric allylation of the 8-benzyloxy-substituted dihydroisoquinoline and by the acid-catalyzed transannulation of the resulting 10-membered lactam.

Graphical abstract: Asymmetric formal synthesis of schulzeines A and C

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Article information

DOI
https://doi.org/10.1039/C2OB25772F
Article type
Communication
Submitted
23 Apr 2012
Accepted
30 May 2012
First published
01 Jun 2012

Org. Biomol. Chem., 2012,10, 5202-5204

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Asymmetric formal synthesis of schulzeines A and C

J. Jang, J. Jung, J. Ahn, J. Sim, D. Chang, D. Kim and Y. Suh, Org. Biomol. Chem., 2012, 10, 5202 DOI: 10.1039/C2OB25772F

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