Total synthesis of (±)-platencin

Takehiko Yoshimitsu, Shoji Nojima, Masashi Hashimoto, Tetsuaki Tanaka

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

A novel route to (±)-platencin is reported, in which the highly stereoselective alkylative quaternization of a cyclohexenone scaffold via 1,4-diastereoinduction and two radical carbon-carbon bond-forming reactions that involve titanium(III)-mediated cyclization and stannyl-radical-mediated skeletal rearrangement are utilized.

Original languageEnglish
Pages (from-to)3698-3701
Number of pages4
JournalOrganic Letters
Volume13
Issue number14
DOIs
Publication statusPublished - Jul 15 2011
Externally publishedYes

Fingerprint

Carbon
carbon
Cyclization
synthesis
Titanium
Scaffolds
titanium
routes
platencin

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Yoshimitsu, T., Nojima, S., Hashimoto, M., & Tanaka, T. (2011). Total synthesis of (±)-platencin. Organic Letters, 13(14), 3698-3701. https://doi.org/10.1021/ol2013439

Total synthesis of (±)-platencin. / Yoshimitsu, Takehiko; Nojima, Shoji; Hashimoto, Masashi; Tanaka, Tetsuaki.

In: Organic Letters, Vol. 13, No. 14, 15.07.2011, p. 3698-3701.

Research output: Contribution to journalArticle

Yoshimitsu, T, Nojima, S, Hashimoto, M & Tanaka, T 2011, 'Total synthesis of (±)-platencin', Organic Letters, vol. 13, no. 14, pp. 3698-3701. https://doi.org/10.1021/ol2013439
Yoshimitsu T, Nojima S, Hashimoto M, Tanaka T. Total synthesis of (±)-platencin. Organic Letters. 2011 Jul 15;13(14):3698-3701. https://doi.org/10.1021/ol2013439
Yoshimitsu, Takehiko ; Nojima, Shoji ; Hashimoto, Masashi ; Tanaka, Tetsuaki. / Total synthesis of (±)-platencin. In: Organic Letters. 2011 ; Vol. 13, No. 14. pp. 3698-3701.
@article{cadd4361d0c14a45bf22c82d29296757,
title = "Total synthesis of (±)-platencin",
abstract = "A novel route to (±)-platencin is reported, in which the highly stereoselective alkylative quaternization of a cyclohexenone scaffold via 1,4-diastereoinduction and two radical carbon-carbon bond-forming reactions that involve titanium(III)-mediated cyclization and stannyl-radical-mediated skeletal rearrangement are utilized.",
author = "Takehiko Yoshimitsu and Shoji Nojima and Masashi Hashimoto and Tetsuaki Tanaka",
year = "2011",
month = "7",
day = "15",
doi = "10.1021/ol2013439",
language = "English",
volume = "13",
pages = "3698--3701",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "14",

}

TY - JOUR

T1 - Total synthesis of (±)-platencin

AU - Yoshimitsu, Takehiko

AU - Nojima, Shoji

AU - Hashimoto, Masashi

AU - Tanaka, Tetsuaki

PY - 2011/7/15

Y1 - 2011/7/15

N2 - A novel route to (±)-platencin is reported, in which the highly stereoselective alkylative quaternization of a cyclohexenone scaffold via 1,4-diastereoinduction and two radical carbon-carbon bond-forming reactions that involve titanium(III)-mediated cyclization and stannyl-radical-mediated skeletal rearrangement are utilized.

AB - A novel route to (±)-platencin is reported, in which the highly stereoselective alkylative quaternization of a cyclohexenone scaffold via 1,4-diastereoinduction and two radical carbon-carbon bond-forming reactions that involve titanium(III)-mediated cyclization and stannyl-radical-mediated skeletal rearrangement are utilized.

UR - http://www.scopus.com/inward/record.url?scp=79960180106&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79960180106&partnerID=8YFLogxK

U2 - 10.1021/ol2013439

DO - 10.1021/ol2013439

M3 - Article

C2 - 21688769

AN - SCOPUS:79960180106

VL - 13

SP - 3698

EP - 3701

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

ER -