Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid

Masafumi Ueda; Sayuri Kawai; Masataka Hayashi; Takeaki Naito; Okiko Miyata

doi:10.1021/jo902540x

Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid

J Org Chem. 2010 Feb 5;75(3):914-21. doi: 10.1021/jo902540x.

Authors

Masafumi Ueda¹, Sayuri Kawai, Masataka Hayashi, Takeaki Naito, Okiko Miyata

Affiliation

¹ Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.

PMID: 20063853
DOI: 10.1021/jo902540x

Abstract

A new efficient synthesis of 2-substituted tetrahydroquinolines has been achieved by the domino reaction of N-indanyl(methoxy)amines, which consists of three types of reactions: elimination of an alcohol, the rearrangement of an aryl group, and the addition of an organolithium or magnesium reagent. The synthetic utility of this approach is demonstrated by the stereoselective formal synthesis of (+/-)- martinellic acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Catalysis
Lithium / chemistry*
Magnesium / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Quinolines / chemical synthesis*
Quinolines / chemistry
Stereoisomerism

Substances

Organometallic Compounds
Pyrroles
Quinolines
martinellic acid
Lithium
1,2,3,4-tetrahydroquinoline
Magnesium