Asymmetric formal synthesis of schulzeines A and C

Jaebong Jang; Jong Wha Jung; Jaeseung Ahn; Jaehoon Sim; Dong Jo Chang; Dae Duk Kim; Young Ger Suh

doi:10.1039/c2ob25772f

Asymmetric formal synthesis of schulzeines A and C

Jaebong Jang, Jong Wha Jung, Jaeseung Ahn, Jaehoon Sim, Dong Jo Chang, Dae Duk Kim, Young Ger Suh

Seoul National University

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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.

Original language	English
Pages (from-to)	5202-5204
Number of pages	3
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	27
DOIs	https://doi.org/10.1039/c2ob25772f
State	Published - 21 Jul 2012

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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.",

author = "Jaebong Jang and Jung, {Jong Wha} and Jaeseung Ahn and Jaehoon Sim and Chang, {Dong Jo} and Kim, {Dae Duk} and Suh, {Young Ger}",

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T1 - Asymmetric formal synthesis of schulzeines A and C

AU - Jang, Jaebong

AU - Jung, Jong Wha

AU - Ahn, Jaeseung

AU - Sim, Jaehoon

AU - Chang, Dong Jo

AU - Kim, Dae Duk

AU - Suh, Young Ger

PY - 2012/7/21

Y1 - 2012/7/21

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84862881401&partnerID=8YFLogxK

U2 - 10.1039/c2ob25772f

DO - 10.1039/c2ob25772f

M3 - Article

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AN - SCOPUS:84862881401

SN - 1477-0520

VL - 10

SP - 5202

EP - 5204

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 27

ER -

Asymmetric formal synthesis of schulzeines A and C

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