Enantioselective Total Synthesis of (-)-Misramine

Keisuke Yoshida, Yuta Fujino, Yusei Takamatsu, Kohei Matsui, Akihiro Ogura, Yuri Fukami, Shinji Kitagaki, Ken-Ichi Takao

Research output: Contribution to journal › Article

1 Citation (Scopus)

Abstract

The enantioselective total synthesis of an unusual pentacyclic proaporphine alkaloid, (-)-misramine, was achieved. The synthetic strategy relied on an enantioselective intramolecular Friedel-Crafts-type 1,4-addition using an asymmetric organocatalyst to construct a spiroindane skeleton containing an all-carbon quaternary stereocenter and a double reductive amination of the keto-aldehyde to form a piperidine ring toward the end of the synthesis. This work is the first example of asymmetric synthesis of a proaporphine alkaloid.

Original languageEnglish
Pages (from-to)5044-5047
Number of pages4
JournalOrganic Letters
Volume20
Issue number16
DOIs
Publication statusPublished - 2018 Aug 17

Fingerprint

Alkaloids
alkaloids
Amination
synthesis
Skeleton
Aldehydes
piperidine
Carbon
aldehydes
musculoskeletal system
vehicles
carbon
rings

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Yoshida, K., Fujino, Y., Takamatsu, Y., Matsui, K., Ogura, A., Fukami, Y., ... Takao, K-I. (2018). Enantioselective Total Synthesis of (-)-Misramine. Organic Letters, 20(16), 5044-5047. https://doi.org/10.1021/acs.orglett.8b02198

Enantioselective Total Synthesis of (-)-Misramine. / Yoshida, Keisuke; Fujino, Yuta; Takamatsu, Yusei; Matsui, Kohei; Ogura, Akihiro; Fukami, Yuri; Kitagaki, Shinji; Takao, Ken-Ichi.

In: Organic Letters, Vol. 20, No. 16, 17.08.2018, p. 5044-5047.

Research output: Contribution to journal › Article

Yoshida, K, Fujino, Y, Takamatsu, Y, Matsui, K, Ogura, A, Fukami, Y, Kitagaki, S & Takao, K-I 2018, 'Enantioselective Total Synthesis of (-)-Misramine', Organic Letters, vol. 20, no. 16, pp. 5044-5047. https://doi.org/10.1021/acs.orglett.8b02198
Yoshida K, Fujino Y, Takamatsu Y, Matsui K, Ogura A, Fukami Y et al. Enantioselective Total Synthesis of (-)-Misramine. Organic Letters. 2018 Aug 17;20(16):5044-5047. https://doi.org/10.1021/acs.orglett.8b02198
Yoshida, Keisuke ; Fujino, Yuta ; Takamatsu, Yusei ; Matsui, Kohei ; Ogura, Akihiro ; Fukami, Yuri ; Kitagaki, Shinji ; Takao, Ken-Ichi. / Enantioselective Total Synthesis of (-)-Misramine. In: Organic Letters. 2018 ; Vol. 20, No. 16. pp. 5044-5047.
@article{af26290bdf43471fbade107726284694,
title = "Enantioselective Total Synthesis of (-)-Misramine",
abstract = "The enantioselective total synthesis of an unusual pentacyclic proaporphine alkaloid, (-)-misramine, was achieved. The synthetic strategy relied on an enantioselective intramolecular Friedel-Crafts-type 1,4-addition using an asymmetric organocatalyst to construct a spiroindane skeleton containing an all-carbon quaternary stereocenter and a double reductive amination of the keto-aldehyde to form a piperidine ring toward the end of the synthesis. This work is the first example of asymmetric synthesis of a proaporphine alkaloid.",
author = "Keisuke Yoshida and Yuta Fujino and Yusei Takamatsu and Kohei Matsui and Akihiro Ogura and Yuri Fukami and Shinji Kitagaki and Ken-Ichi Takao",
year = "2018",
month = "8",
day = "17",
doi = "10.1021/acs.orglett.8b02198",
language = "English",
volume = "20",
pages = "5044--5047",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

T1 - Enantioselective Total Synthesis of (-)-Misramine

AU - Yoshida, Keisuke

AU - Fujino, Yuta

AU - Takamatsu, Yusei

AU - Matsui, Kohei

AU - Ogura, Akihiro

AU - Fukami, Yuri

AU - Kitagaki, Shinji

AU - Takao, Ken-Ichi

PY - 2018/8/17

Y1 - 2018/8/17

N2 - The enantioselective total synthesis of an unusual pentacyclic proaporphine alkaloid, (-)-misramine, was achieved. The synthetic strategy relied on an enantioselective intramolecular Friedel-Crafts-type 1,4-addition using an asymmetric organocatalyst to construct a spiroindane skeleton containing an all-carbon quaternary stereocenter and a double reductive amination of the keto-aldehyde to form a piperidine ring toward the end of the synthesis. This work is the first example of asymmetric synthesis of a proaporphine alkaloid.

AB - The enantioselective total synthesis of an unusual pentacyclic proaporphine alkaloid, (-)-misramine, was achieved. The synthetic strategy relied on an enantioselective intramolecular Friedel-Crafts-type 1,4-addition using an asymmetric organocatalyst to construct a spiroindane skeleton containing an all-carbon quaternary stereocenter and a double reductive amination of the keto-aldehyde to form a piperidine ring toward the end of the synthesis. This work is the first example of asymmetric synthesis of a proaporphine alkaloid.

UR - http://www.scopus.com/inward/record.url?scp=85051698040&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85051698040&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b02198

DO - 10.1021/acs.orglett.8b02198

M3 - Article

VL - 20

SP - 5044

EP - 5047

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 16

ER -

Access to Document