Construction of the Azacyclic Core of Tabernaemontanine-Related Alkaloids via Tandem Reformatsky-Aza-Claisen Rearrangement

Young Ger Suh; Changjin Lim; Jaehoon Sim; Jae Kyun Lee; Young Joon Surh; Seung Mann Paek

doi:10.1021/acs.joc.6b02648

Construction of the Azacyclic Core of Tabernaemontanine-Related Alkaloids via Tandem Reformatsky-Aza-Claisen Rearrangement

Young Ger Suh^*
, Changjin Lim
, Jaehoon Sim
, Jae Kyun Lee
, Young Joon Surh
, Seung Mann Paek

^*Corresponding author for this work

Department of Pharmacy

Seoul National University
Korea Institute of Science and Technology
Gyeongsang National University

Research output: Contribution to journal › Journal article › peer-review

9 Scopus citations

Abstract

A divergent synthetic methodology for a tabernaemontanine-related alkaloid was developed. The synthetic route features practical improvements in the Pictet-Spengler cyclization for the tetrahydro-β-carboline intermediate and an unprecedented tandem Reformatsky-aza-Claisen rearrangement to create the core carbon skeleton and stereochemistries of tabernaemontanine-related alkaloids.

Original language	English
Pages (from-to)	1464-1470
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	82
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.6b02648
State	Published - 2017.02.3

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10.1021/acs.joc.6b02648

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title = "Construction of the Azacyclic Core of Tabernaemontanine-Related Alkaloids via Tandem Reformatsky-Aza-Claisen Rearrangement",

abstract = "A divergent synthetic methodology for a tabernaemontanine-related alkaloid was developed. The synthetic route features practical improvements in the Pictet-Spengler cyclization for the tetrahydro-β-carboline intermediate and an unprecedented tandem Reformatsky-aza-Claisen rearrangement to create the core carbon skeleton and stereochemistries of tabernaemontanine-related alkaloids.",

author = "Suh, \{Young Ger\} and Changjin Lim and Jaehoon Sim and Lee, \{Jae Kyun\} and Surh, \{Young Joon\} and Paek, \{Seung Mann\}",

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AU - Suh, Young Ger

AU - Lim, Changjin

AU - Sim, Jaehoon

AU - Lee, Jae Kyun

AU - Surh, Young Joon

AU - Paek, Seung Mann

PY - 2017/2/3

Y1 - 2017/2/3

N2 - A divergent synthetic methodology for a tabernaemontanine-related alkaloid was developed. The synthetic route features practical improvements in the Pictet-Spengler cyclization for the tetrahydro-β-carboline intermediate and an unprecedented tandem Reformatsky-aza-Claisen rearrangement to create the core carbon skeleton and stereochemistries of tabernaemontanine-related alkaloids.

AB - A divergent synthetic methodology for a tabernaemontanine-related alkaloid was developed. The synthetic route features practical improvements in the Pictet-Spengler cyclization for the tetrahydro-β-carboline intermediate and an unprecedented tandem Reformatsky-aza-Claisen rearrangement to create the core carbon skeleton and stereochemistries of tabernaemontanine-related alkaloids.

UR - https://www.scopus.com/pages/publications/85011319815

U2 - 10.1021/acs.joc.6b02648

DO - 10.1021/acs.joc.6b02648

M3 - Journal article

C2 - 28051867

AN - SCOPUS:85011319815

SN - 0022-3263

VL - 82

SP - 1464

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Construction of the Azacyclic Core of Tabernaemontanine-Related Alkaloids via Tandem Reformatsky-Aza-Claisen Rearrangement

Abstract

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